Sure, we don’t get the big leaf-changing display or chilly sweater weather, but as the summer heat and humidity finally ease up, locals come back out in full force. September through November is the start of festival season here. It’s when we can spend more time outside, enjoying live music, waterfront sunsets, and all the arts, food, festivals, and events in Venice and the surrounding areas that make life here so enjoyable.

For locals, this season feels like we’re reclaiming our outdoor spaces after summer. The streets come alive, with something happening every weekend, and it’s a great time to enjoy the area before the busy winter visitors arrive. And for anyone visiting during this time, it’s the perfect opportunity to get an authentic taste of the region, the local culture, and the welcoming community vibe that makes Southwest Florida so special.

We’ve rounded up all the best seasonal concerts, markets, family-friendly activities, festivals, and events happening in Venice, Wellen Park, and nearby spots like Sarasota, Punta Gorda, Fort Myers, Bradenton, St. Petersburg, and Tampa. Whether you’re new to the area, a longtime local, or planning a fall break, these events will get you out exploring and experiencing that Southwest Florida community vibe.

** PLANNING AHEAD FOR THE SEASONS? CHECK OUT OUR GUIDE FOR THE BEST WINTER EVENTS IN VENICE AND BEYOND. 

Venice, Florida Fall Festivals and Events

Venice is packed with things to do all year long, but fall marks the start of festival season, bringing a whole new energy to the area’s already lively calendar. 

Recurring & Regular Events in Venice, FL

From longtime favorites like the Venice Farmers Market and Friday Night Concerts in the Park to seasonal festivities like Haunted History tours and the Downtown Halloween Strut, something is happening nearly every weekend.

Venice Centennial 2025 — The City Turns 100

2025 marks a milestone for this little slice of paradise — Venice is turning 100 years old! The city plans to spread the celebrations over 18 months, incorporating events, art installations, lectures, contests, and surprises into the regular festival calendar.

The Centennial kicks off this fall with the 2025 Holiday Parade & “All Aboard the Centennial” theme on November 29, 2025, in downtown Venice. 

Over the coming months, you can look forward to special events, including “Together Through Time: Venice at 100” (a gala dinner and program), the unveiling of the John Nolen statue, and new art installations throughout the town. The Venice Centennial Lecture Series and exhibits like Venice Turns 100! will run regularly at the Venice Museum & Archives and in local libraries. 

The city is also seeking community involvement, partnerships, and volunteer opportunities to help shape and celebrate the Centennial.  Additionally, you’ll see some of your favorite festivals receive a little extra sparkle, and new celebrations will be added to the mix. (We’ll be keeping an eye on updates and dropping them into your calendar!)

Major Fall Events in Venice, FL

In addition to the regular calendar lineup, here are the signature fall events in Venice (the ones locals and visitors look forward to every year).

Sun Fiesta October 17–19, 2025

The iconic Sun Fiesta is Venice’s biggest fall tradition, and one of the most beloved community festivals in all of Southwest Florida. You’ll find a huge arts & crafts fair, live music on stage throughout the weekend, food and drink vendors, a lively parade, and even the famous bed races down Venice Avenue.

This event has been running strong since 1994 and has become one of the most anticipated October events in Venice, and it’s still offering free admission (yes, thank you!). It’s the perfect blend of small-town charm and big-festival fun, all for good causes within the community. Parking can be tight downtown, so consider arriving early or carpooling with friends.

Haunted 5K, 10K, Half & Full Marathon October 4, 2025

Get your running shoes (and costumes) ready for this spooky-fun race series. Whether you’re a serious runner or just in it for the medal and the memories, the Haunted Run features scenic courses, themed gear, and plenty of Halloween spirit.

Downtown Venice Halloween Strut October 31, 2025

This is one of the most family-friendly Halloween traditions in the area. Kids (and often adults) in costume parade through downtown as local businesses hand out candy. It just doesn’t get much more wholesome and fun than that. Expect music, decorated storefronts, and plenty of photo-worthy moments.

37th Annual Downtown Venice Art Festival November 1–2, 2025

Every fall, the streets of downtown Venice turn into an open-air art gallery. Hosted by Howard Alan Events and Venice MainStreet, this juried festival showcases artists from across the country. You can find everything from fine art and photography to ceramics, jewelry, and home décor.

It’s free to attend and is a great place to start your holiday shopping early or pick up something unique for your home.

** WANT MORE SEASONAL FUN? DON’T MISS OUR GUIDE TO SPRING EVENTS IN VENICE.

Wellen Park Fall Events

If you haven’t experienced a Wellen Park event, you’re in for a treat this fall! This neighborhood has genuinely become one of the area’s go-to community hubs. As the weather cools down, the entire area comes alive with festive lights, outdoor concerts, seasonal markets, and family-friendly gatherings.

The heart of it all is Downtown Wellen, where you can stroll by the lake, grab a bite at one of the restaurants, and enjoy the laid-back but lively vibe. Whether you’re here for holiday celebrations, a weekend market, or just an evening of live music under the stars, Wellen Park knows how to make fall feel special.

Here are some of our top Wellen Park event picks for the season:

Regular Weekly & Monthly Fun at Wellen Park

• DJ Nights at The Yard — Come from Monday til Wednesday evenings for laid-back music vibes.
• Serenade in the Shade — Thursday through Saturday offers up ambient acoustic sessions under the Heritage Tree.
• Friday Night Live Concerts — Outdoor music with food trucks and a lively community feel. Classic way to kick off the weekend.
• Sunday Groove at the Farmers Market — Chill Sunday tunes while you shop for fresh goodies.
• Monthly Dueling Pianos (3rd Thursday) — A crowd-pleaser at Solis Hall, which is always a fun, interactive night.

These regular happenings make it easy to enjoy Wellen Park on any given week. But this neighborhood keeps on giving. In addition to the regular lineup of events, Wellen Park will also host some epic seasonal entertainment. Our top picks are listed below. 

Bigger Seasonal/Fall Wellen Park Events

Oktoberfest at Wellen Park, October 4, 2025

This fall favorite features polka music, bratwurst, beer tents, and classic Oktoberfest games, including the stein-hoisting contest. It’s lively, festive, and perfect for the whole family. This is the second year it has run, and it is set to be an annual favourite in the area. It’s free admission and at the top of our list for not-to-be-missed fun events in Southwest Florida. 

Wellen Park Spooktacular Halloween, October 31, 2025

This is exactly what it says on the tin – a kid-friendly Halloween celebration with trick-or-treating at local shops. But in true Wellen Park style, it’s even more fun with a live DJ, plenty of seasonal treats, and even a dog costume contest! You better believe our pooch, Hana, is excited about entering this, and boy, is she in it to win it! We might even be tempted to share a sneak peek of her costume on our social media page, so be sure to follow us to catch it. 

Wellen Park Wine Festival November 14–15, 2025

If you love wine, food, and good company, the Wellen Park Wine Festival is the event of the season. It kicks off on Friday, November 14, with the elegant ‘Five-Course Dinner with an Exclusive First Taste’ at Solis Hall. This intimate, upscale evening will feature perfectly paired culinary creations and pours from acclaimed vintners and is expected to sell out quickly. Gosh, it even sounds fancy in writing!

The Saturday offers a full day of wine-themed fun and education, including a Wine Class 101 and the main event, the ‘Grand Tasting’, with nearly 40 vintners, local food tents, and live entertainment. Tickets are essential, and as well as general admission, there is both a VIP option and designated driver reduction (Our commiserations if you’re on driving duty this time – we recommend you leave the car at home so you can join in on the delicious tasting!)

Thanks4Giving Tree Campaign October 5 – November 14, 2025

This community-driven program invites residents and visitors to donate grocery gift cards, which are distributed to local families in need. The initiative is run in partnership with Wellen Park Rotary Club and aims to feed over 100 local families. 

It’s so simple to get involved: collect a gift tag from the tree in the Wellen Park Welcome Center (each one represents a family they hope to support), purchase a Publix gift certificate in the mount of your choosing (so great that there is no minimum amount so anyone can offer whatever they can), return your donation to the welcome center where your tag is hung on the tree to show festive progress. At the end of the campaign dates, meal packages are purchased and supplied to the number of families on the tag tree. It’s a great community project and a heartwarming way to give back to the local community during the season.

5th Annual Grilled Cheese Festival,  November 22, 2025

Cheese lovers, assemble! The Grilled Cheese Festival returns to CoolToday Park (the Braves’ Spring Training stadium in Wellen Park) for a full day of melty goodness, craft beer, and live music on the plaza. It’s free and family-friendly, with food trucks serving creative grilled-cheese combos (from classic melts to loaded gourmet builds), a beer garden with souvenir mugs, kids’ activities, and music. Festival hours run 11 AM til 6 PM. Our  advice: come hungry and pace yourself.

This day has become a little tradition for us when we celebrate our love of beer and grilled cheese… and Josh loads up on Braves Spring Training tickets. Single-game tickets are released on this day, so head over to grab your fill of cheese and baseball!

If you want to get a sneak peek inside the stadium then check out our video on Braves Spring Training at CoolToday Park . It’s one of our favorite behind-the-scenes looks at this Wellen Park gem.

Nearby Southwest Florida Festivals & Events

If you’re up for a little road trip (and who isn’t?), there’s plenty of fall fun just beyond Venice.

Fall Events in Sarasota

Sarasota Rocktoberfest October 17–19, 2025

Get ready to raise a glass at Sarasota Rocktoberfest, one of the most fun and festive fall events in Sarasota. This three-day celebration takes over downtown Sarasota with free live music, fantastic food, and refreshing drinks throughout the weekend.

Whether you’re there to enjoy the outdoor beer garden, shop the local vendor market, or soak in the laid-back Florida fall vibes, there’s something for everyone. The event is both family-friendly and dog-friendly, so bring your crew (including furry friends) and make a day of it.

Expect a lively mix of rock, pop, and local bands performing throughout the weekend, along with a variety of German-inspired dishes and regional favorites. It’s one of the easiest and most affordable ways to kick off festival season in Sarasota.

29th Annual Downtown Sarasota Craft Festival October 18–19, 2025

If you love handmade art, local talent, and a relaxed weekend stroll, the Downtown Sarasota Craft Festival is a must-do this fall. Held at 5 Points Park in the heart of downtown, this long-running event fills the streets with creativity, color, and a sense of community charm.

Now celebrating its 29th year, the festival showcases a diverse array of handcrafted treasures, including jewelry, ceramics, photography, paintings, clothing, and home décor. You’ll also find an inviting Green Market, where you can browse artisanal goods, including handmade soaps, gourmet spices, and tropical plants.

Admission is free, and the atmosphere is perfect for a weekend outing, making it easy to explore at your own pace with plenty of cafés, shops, and restaurants nearby. 

Water Lantern Festival October 25,  2025

The Water Lantern Festival at Nathan Benderson Park is one of the most magical fall events in Southwest Florida. Each October, this 600-acre lakeside park transforms into a breathtaking scene as hundreds of hand-decorated glowing lanterns drift across the water, each one carrying personal messages of love, hope, and remembrance.

It’s a beautiful, family-friendly evening filled with food trucks, live music, and a sense of calm community connection. Kids under eight get in free with a paid adult ticket (lanterns sold separately), and tickets often sell out early.

After the lanterns have floated away, keep the night going by grabbing dinner or drinks in town, or heading to PopStroke for a round of mini-golf under the lights.

Gulfcoast Pride Festival, October 25, 2025

Get ready for a burst of color and celebration at the Gulfcoast Pride Festival, held each fall in Sarasota’s vibrant Rosemary District downtown. Known as one of the fastest-growing LGBTQ+ events on Florida’s Gulf Coast, this festival literally fills the streets with energy, music, and community pride.

The event hosts more than 100 local vendors offering pride-themed goods, art, and handmade items, along with performances from both local and national entertainers. There’s no shortage of delicious food either, as the area’s restaurants and food artisans line the streets with a wide variety of mouthwatering treats.

Repticon Sarasota, October 25, 2025

Calling all reptile fans: Repticon Sarasota slithers back into town at the end of October, bringing with it a fascinating mix of scaly, slinky, and totally cool creatures. This family-friendly expo is part trade show, part educational adventure, and 100% fun for anyone who loves animals.

You’ll find vendors from all over Florida showcasing reptiles, amphibians, and exotic pets, plus everything you could ever need to care for them, from enclosures and feeders to unique reptile-themed merch. Even if you’re not planning to take home a new scaly friend, it’s a great way to learn about these amazing animals up close.

Tickets are incredibly affordable, starting at just $12 for adults and $6 for kids, with free admission for children 4 years and under. Each ticket is valid for all-day entry on either Saturday or Sunday.

Lights at Spooky Point October 3 – November 1, 2025

If you’re looking for something a little spooky but still totally family-friendly this fall, Lights at Spooky Point at Selby Gardens’ Historic Spanish Point campus in Osprey is the perfect pick. Every October, the gardens transform into a glowing Halloween dreamscape filled with twinkling lights, creative displays, and just the right amount of “boo.”

It’s a ticketed event with two entry times every day, so there’s plenty of opportunity to fit it into your schedule. Once there, you can wander the paths under the stars, spot pumpkins and ghosts tucked among the trees, and enjoy all the cozy Halloween vibes without the jump scares. It’s fun, festive, and gorgeous, especially when the lights reflect off the bay.

Pro tip: arrive early to explore the gardens in daylight, then stay around after dark to watch the whole place come alive. It’s a little eerie, a little magical, and a whole lot of fun.

Siesta Key Crystal Classic November 14–17, 2025

Fun on the beach isn’t just for summer! Every November, Siesta Beach turns into an outdoor art gallery as sand sculptors from all over the world compete in the Annual Siesta Key Crystal Classic Sand Sculpting Festival. Over four incredible days, 24 artists transform piles of that famous white Siesta Key sand into jaw-dropping masterpieces. Some of the displays are so impressive that they really make you forget they’re made from sand at all.

The festival isn’t just for watching, though. Spectators can join workshops, take sand-sculpting lessons, enjoy live music under the tent, and browse through 75 vendors at the Vendor Village, where they can find a variety of food, drinks, and souvenirs. On Saturday night, stick around for Sculptures After Dark, when the illuminated sculptures glow under colorful lights. It’s pure beachside magic.

If you’re feeling creative yourself, sign up for the Amateur Competition or cheer on contestants during the high-energy Quick Sand Contest. And don’t miss the Awards Ceremony on Sunday at 3 PM, when the top artists are crowned. It’s family-friendly, full of talent, and just the right blend of beach fun and artistic awe.

Sarasota Medieval Fair Weekends, November 1–30, 2025

Step into a world where history and pageantry collide at the Sarasota Medieval Fair, held under the sprawling oaks of The Woods of Mallaranny in Myakka City. Every weekend in November, this 50-acre fairground transforms into a lively medieval village filled with jousting knights, jesters, minstrels, belly dancers, and all the merriment you’d expect from a true Renaissance celebration.

Now celebrating its 21st anniversary, the fair is bigger and better than ever, with over 140 artisan shops, 14 performance stages, and an ever-changing lineup of entertainment. Each weekend brings a unique theme and a fresh roster of shows, so there’s something new to experience every time you visit.

Families can enjoy rides, games, and the Children’s Realm, while foodies will love the turkey legs, hearty feasts, and frothy ales that make the fairgrounds smell downright irresistible. Between the full-contact jousts, human chess matches, and endless live music, it’s easy to spend the whole day getting lost in the fun.

Tickets are flexible and easy to plan around, as you can grab a single-day ticket for any Saturday or Sunday, or make the most of the season with a multi-day flex pass, allowing you to experience all five weekends of fun. Since each weekend has its own theme and special lineup, the flex pass is a great way to catch it all.

Whether you’re a history buff, a fantasy fan, or just someone who loves a good themed festival, the Sarasota Medieval Fair is one of fall’s most unforgettable adventures and a highlight of fall events in Sarasota.

Lakewood Ranch Blues Festival December 6, 2025

After an unforgettable 2024 event, the Lakewood Ranch Blues Festival is gearing up for another soulful, high-energy weekend this fall, and the 2025 lineup is looking incredible. Expect two full days of live performances from some of the best blues artists around, along with delicious food, local vendors, and that laid-back, toe-tapping community vibe that makes this festival such a favorite.

The event brings together crowd-pleasing favorites and fresh new acts, all set against the welcoming backdrop of Waterside Place in Lakewood Ranch. Grab a drink, pull up a lawn chair, and settle in for great music, great food, and plenty of friendly faces.

Events in Punta Gorda this Fall

Englewood Beach Waterfest October 11–12, 2025

Get ready for high-speed thrills and beachside fun at Englewood Beach Waterfest, host of the APBA Offshore World Championship races on Saturday, October 11, and Sunday, October 12, 2025. This is the weekend when the Gulf roars as multiple classes of racing powerboats compete. According to the Race Weekend page, general admission tickets cover both full days of racing, so you won’t need to re-buy for Sunday. 

While the powerboats roar through the waves, on the sand you’ll find a Beach Oasis & Food Court with tents offering regional favorites, festival staples (think funnel cakes, popcorn, pretzels, ice cream), and a “Raceday cocktail” special for those who want something extra.

There’s also a Family Conservation Center, which is excellent for teaching kids (and adults!) about our marine and coastal ecosystems. If you’re into marine and conservation programming, that’s a fun stretch between races.

The festival kicks off with a Block Party on Friday, October 10, 2025, free to the public, held at Dignam Family Stage at Pioneer Plaza, as a fun warm-up to the racing weekend. 

7th Annual International Culture Fest, October 25, 2025

Take a trip around the world without ever leaving Punta Gorda at the 7th Annual International Culture Fest. This family-friendly celebration, taking place from 12 PM to 6 PM, invites guests to experience the beauty and diversity of cultures from around the globe, all in one vibrant waterfront setting.

You’ll find international cuisine, cultural crafts, and live performances representing traditions from around the world. Kids (and adults!) can join in educational activities and creative workshops while browsing local artisan booths and sampling flavors from around the world.

Presented by the Cultural Heritage Center of Southwest Florida, this event celebrates the region’s rich cultural mix, fostering connection, curiosity, and community joy.

Florida International Air Show — November 1–2, 2025

Get ready to look up — the Florida International Air Show is soaring back into Punta Gorda Airport this fall, filling the skies with roaring engines, precision maneuvers, and a whole weekend of aviation excitement. 

Gates open at 9 AM, and the flying kicks off at 12 PM, giving you plenty of time to explore the static displays, food vendors, and family exhibits before the show starts.

Now in its 44th year, this event features some of the world’s best pilots and aerial acts, including the U.S. Navy Blue Angels and the F-16 Viper Demo Team, vintage warbirds, and crowd-pleasing stunt pilots. On the ground, you’ll find everything from aviation education booths to up-close aircraft displays and kid-friendly activities in the Family Aviation Experience area.

There are ticket options to suit everyone. General admission is ideal for families and first-time attendees who seek the classic festival experience. At the same time, upgraded options include Flightline Club seating for shaded comfort and catered food, Photo Pit access for photographers looking to capture the best shots, and VIP Pavilion tickets for an all-inclusive experience featuring prime views and premium amenities. Kids 3 and under get in free, making it an excellent outing for families.

Holiday Lighting of the Village “Jingle & Jammies” November 15, 2025

The most anticipated event of the year in Punta Gorda is back, and this year’s theme is all about cozy cheer! The Holiday Lighting of the Village at Fishermen’s Village kicks off the holiday season with twinkling lights, festive fun, and a brand-new theme: “Jingle & Jammies.” Families are encouraged to arrive in their cutest and coziest pajamas for a night filled with contests, photo opportunities, and holiday magic.

Enjoy live music, Santa’s grand arrival, and the official Lighting of the Village. Shops stay open late, offering complimentary holiday treats while you browse for gifts and soak in the small-town magic of a Florida Christmas by the water.

Fall Festivals & Events in Fort Myers 

Edison & Ford Fall Festival October 18, 2025

Edison & Ford Winter Estates in Fort Myers hosts this lovely Fall Festival on Saturday, October 18, from 9 AM to 4 PM. The festival is free to attend (although some activities carry a small additional fee), offering a relaxed mix of crafts, music, food, and seasonal fun. For a little extra adventure, you can climb the historic Banyan Tree or pick out a pumpkin. 

Note that admission to the museum buildings, laboratory, and riverside areas of the property requires a separate ticket.

If you’re making a weekend of your travels, this event offers a nice blend of heritage, art, laid-back vibes, and local flavor, especially if you’re looking for something a little more low-key than the big festivals.

BIG ARTS Film Festival November 14–15, 2025

If you’re looking for a cinematic experience that feels both intimate and inspiring, make your way to Sanibel Island for the BIG ARTS Film Festival, a two-day celebration of film combining artistry, conversation, and community in a way only BIG ARTS can deliver.

The weekend includes exclusive screenings, live Q&As, and special gatherings where film lovers can connect with the creative minds behind the stories. Between screenings, guests can enjoy an opening reception, meet the filmmaker, and participate in discussions that illuminate how storytelling shapes our understanding of the world. It’s thoughtful, creative, and deeply human—the kind of event that reminds you why the arts matter and just how prominent they are in this creative corner of Florida. 

Fall Events in Tampa

Oktoberfest Tampa October 10–12, 2025

If you’re in Tampa this fall, don your lederhosen (or comfy jeans) and head downtown for Oktoberfest Tampa, held along the Hillsborough River at Curtis Hixon Waterfront Park. This annual celebration is one of the largest and most festive Oktoberfests in the region, marking its 16th annual appearance in 2025. 

Across three days, the festival is packed with authentic German cheer, live music, dancing, and Bavarian food & drink. You’ll find beer tents serving everything from Märzen to hefeweizen, along with traditional German eats like pretzels, sausages, and schnitzel. It’s a full-on German village vibe, right in the heart of Tampa. 

Fun competitions, such as Mr. & Mrs. Oktoberfest and a Beard & Mustache contest, take place during the festival, and stein-hoisting challenges keep things lively and entertaining. Oktoberfest Tampa is a Tampa fall event worth adding to your calendar.

Tampa Pig Jig October 18, 2025

What started as a friendly backyard barbecue competition has grown into a massive annual fundraiser and live music festival set against the beautiful backdrop of Julian B. Lane Riverfront Park in downtown Tampa.

This year’s lineup features nationally recognized country and rock artists, including Megan Moroney, Midland, and Matt Nathanson, promising a full day of good tunes and good vibes. Between sets, you can sample BBQ from the corporate cook-off, sip ice-cold drinks, play games, and hang out with the friendliest crowd in Tampa Bay.

Best of all, every bite and every beat supports a great cause, as proceeds benefit NephCure Kidney International, helping to fund research and raise awareness for rare kidney diseases.

Ford Taste of Latino Festival, October 26, 2025

Spice up your fall weekend with a trip to Historic Ybor City for the 7th Annual Ford Taste of Latino Festival at Centennial Park. This free, family-friendly celebration takes place from 12 PM to 6 PM. It brings together the best of Latin music, dance, food, and art for an unforgettable afternoon.

You’ll find live music and cultural performances filling the park, along with booths serving up authentic Latin flavors from across the Americas — think empanadas, tacos, pastelitos, and more. Local artists and vendors line the walkways, adding color and creativity to every corner.

Don’t miss the TOP Latino Chef Contest, where talented chefs compete for culinary bragging rights, or the Florida Latino & Latina Lideres Recognition Ceremony, honoring community leaders who make a difference across the state.

It’s the perfect Sunday outing to celebrate culture, community, and cuisine right in the heart of Tampa Bay this fall.

Hillsborough County Fair October 30 – November 9, 2025

Nothing says fall in Florida quite like the Hillsborough County Fair. It’s eleven full days of rides, music, food, and good old-fashioned family fun. Held at the Hillsborough County Fairgrounds, this annual event brings the community together with a little something for everyone.

Expect all your favorite fair attractions, from thrilling rides and delicious food (hello, funnel cakes and corn dogs!) to live shows and local competitions, along with special themed events throughout the week. Highlights include Rodeo Weekend, goat yoga, and interactive agricultural exhibits that celebrate the county’s farming roots.

From livestock shows and arts displays to nightly entertainment and a midway full of lights and laughter, it’s a fall tradition that captures everything we love about small-town fairs with a Florida twist.

Tampa Tattoo Arts Convention November 7 – 9, 2025

If you love art with an edge (or you’re thinking about adding to your own collection), the Tampa Tattoo Arts Convention is the place to be. Hosted by Villain Arts, this massive three-day event brings together hundreds of tattoo artists from around the country to showcase their unique styles, from fine-line and realism to bold traditional work.

The weekend features live entertainment, including sideshow acts, circus performers, and even a contortionist archer (yep, you read that right). You can browse vendors selling art, jewelry, and alternative fashion, or even enter a tattoo contest to show off your ink and compete for a trophy.

Tickets are $20 for a single-day pass or $40 for the entire three-day weekend. Children under 12 are admitted free, making it a fun (and surprisingly family-friendly) way to explore one of Tampa’s most creative and unconventional events.

Events in St Petersburg this Fall

Clearwater Jazz Holiday October 16-19, 2025

Get ready for four days of soulful sounds, waterfront vibes, and community magic at the 46th Clearwater Jazz Holiday, where you’ll be treated to a stacked lineup of headliners and emerging artists across several stages at Coachman Park in downtown Clearwater. Gates open at 4:00 PM on Thursday and Friday, and at 3:00 PM on Saturday and Sunday. 

St. Pete Pier Pumpkin Patch & Fall Festival October 10–19, 2025

Fall comes to life on the waterfront with the St. Pete Pier Pumpkin Patch and St. Pete Fall Fest, turning Spa Beach and Family Park into a seasonal wonderland with free admission. 

Stroll through rows of plump pumpkins (available for purchase), snap photos in rustic settings (complete with hay bales, a vintage truck, and more), and soak up the crisp autumn energy right by the water. 

The patch’s operating hours are variable, so do check before turning up. Beyond the pumpkins, the Fall Festival (on October 18) brings a full day of fun: local vendors, live music, a kids’ zone, face painting, festive décor, and a drone show as the evening highlight. It’s an easy, feel-good fall outing to bring the family (and your pup), meander the pier, pick your pumpkin, enjoy local bites, and catch that autumn glow over Tampa Bay.

Tarpon Springs Seafood Festival November 7–9, 2025

Get your appetite ready for the 37th Annual Tarpon Springs Seafood Festival as it takes over the Sponge Docks for a weekend full of fresh flavors, coastal vibes, and family fun. 

Admission is free, making it accessible to everyone. The festival runs from 12:00 PM to 9:00 PM on Friday and from 10:00 AM to 9:00 PM on Saturday. Saturday, 10 AM–5 PM, and Sunday.  

You’ll find plenty of seafood vendors serving up everything from Gulf shrimp to grilled fish. Of course, there are also non-seafood options available for those who prefer something else. Alongside the food, the event features a chef’s competition, live music throughout the weekend, arts & crafts booths, artisan vendors, and family-friendly activities. 

SAVOR St. Pete Food + Wine Festival November 1–2, 2025

SAVOR St. Pete (aka Savor The Burg) returns to Vinoy Park for two days of mouthwatering delight by the waterfront. This festival is all about enjoying the craft behind food and drink. Think local chefs, national culinary talent, craft beers, wines, spirits, and all the flavors in between. You’ll find a curated Grand Tasting Village full of food & beverage booths, cooking demonstrations, mixology segments, and interactive opportunities for food lovers. This is one of the top food + wine events on Florida’s Gulf Coast and a perfect excuse for a food-loving weekend trip to St. Pete.

SHINE St. Pete Mural Festival November 7 – 16, 2025

St. Petersburg puts on its artistic best each fall with the SHINE Mural Festival, and 2025 marks the 11th anniversary of this city-wide celebration of color, creativity, and community. Over the course of ten days, SHINE brings local, national, and international mural artists to walls all across the city, transforming blank surfaces into bold works of public art. This year, the festival plans to introduce 15 new murals, enhancing St. Pete’s already impressive outdoor art scene. 

Tips for Enjoying Fall Festivals in Southwest Florida

With so many significant events happening this season, a little planning goes a long way toward making the most of your weekend adventures. Whether you’re heading to a beachside concert, a waterfront wine fest, or a small-town fair, these quick tips will help you enjoy the day like a local:

• Arrive early for the big events — parking fills up fast.
• Bring cash; many food vendors still prefer it.
• Pack a lawn chair or blanket for outdoor concerts and movies.
• Check event sites for updates. Schedules sometimes shift due to weather.
• Explore neighborhoods while you’re there.  If you’re considering moving to the area, these events are an excellent way to get a sense of the community.

Which Venice Event Will You Go To This Fall? 

Fall in Southwest Florida is all about community spirit, sunshine, and enjoying the outdoors again after the hot summer. From local favorites to big regional festivals in Sarasota and Tampa, there’s something for everyone nearly every weekend.

This time of year is perfect for making the most of festival season or visiting to explore potential new neighborhoods. You’ll find fall in Venice and the surrounding area to be one of the most vibrant and welcoming times of the year.

Want more local guides? Check out our YouTube videos for real estate insights and fun things to do around Venice.

The post The Best 2025 Fall Festivals and Events in Venice, Wellen Park & Beyond appeared first on That Florida Life.

If you caught our Winter Events Roundup, you already know we love celebrating the seasons in style. Now, we’re back with a fresh list of can’t-miss Spring events in Sarasota, Venice, Wellen Park®, and Southwest Florida so mark your calendars and get ready for food, music, festivals, and more!

Watch the video below to get a roundup of our 6 favorite springtime festivals, or scroll on to read a comprehensive guide of Venice and surrounding area Spring events that you can’t miss.

Venice, Florida Events

Regular and Recurring Events in Venice, Florida

Venice is bursting with things to do all year long—but spring brings a fresh energy to the area’s already vibrant calendar. From daily heritage tours to weekly favorites like yoga on the beach, and monthly outdoor movie screenings, there’s no shortage of ways to spend your days. Here’s just a few of our favorite regular spring events: 

• Venice Farmers Market

Venice Farmer’s Market is held in the heart of downtown Venice, every Saturday. Here, you can discover fresh produce, artisanal goods, and local crafts. It’s a perfect way to support local vendors and enjoy the community atmosphere.​

• Friday Night Concert Series

Every other Friday night, the Centennial Park Gazebo comes alive with free concerts featuring local bands and artists. Bring a chair or blanket and enjoy an evening of music under the stars.​

• Monthly City Bicycle Ride

On the second Thursday of each month at 10:00 AM, the City of Venice organizes a group bicycle ride. Cyclists of all skill levels are welcome to join this leisurely ride, which promotes community engagement and healthy living. The route and meeting point details are typically announced closer to the event date, which you can find here.

• Venice History Tours

Step back in time and uncover the fascinating history of Venice! Whether you’re hopping on a guided golf cart ride, walking through historic downtown with a local expert, or diving into spooky tales on a haunted history tour, there are plenty of ways to discover the stories behind this charming Gulf Coast town. It’s fun for visitors and locals alike, and perfect for springtime meanders in the sunshine . Tour availability varies, as do the prices, so check the tour provider (linked above) for full details.

Major Events in Venice, Florida Spring 2026

Beyond the regular daily and weekly happenings, spring in Venice brings a variety of standout events—some annual favorites, others special one-time celebrations. Here are a few of our top picks from the spring events in Venice, Florida.

Pirate 1M, 5K, 10K, 15K, & Half Marathon (April 4th, 2026)

Runners of all skill levels are invited to join the race at Shamrock Park in Venice, FL. This event offers a series of races, from a fun 1-mile run to the challenging half marathon, making it perfect for all abilities or even a fun family challenge! 

Runners must sign up in advance at RunSignUp and the races start at 8am. The scenic route through the park provides a beautiful backdrop, and costumes are encouraged to add a festive pirate flair to the event. Winners of the best costume prize are announced at the start of the race, and all finishers will receive a themed medal! 

Venice Sharks Tooth Festival (April 11–12, 2026)

Celebrate Venice’s reputation as the “Shark’s Tooth Capital of the World” at Centennial Park for a weekend of fossil and beach-inspired fun. You’ll find vendors, live music, and delicious food. 

Although this event technically falls under Spring, it’s so much fun that we gave you a heads-up in our Winter events roundup to make sure you had plenty of time to mark it in your calendar! It’s one of the best events in Venice all year. 

Venice’s beaches are famous for their abundance of fossilized shark teeth, attracting enthusiasts from all over the world. The area’s unique geological history has created a rich deposit of these fossils along its shores, some of which we share on our YouTube video here.

This free, family-friendly festival offers a variety of fun activities for all ages. There’s an interactive shark-themed play area for kids (sorry, grown-ups!), which includes face painting, shark tooth hunting, and much more. 

While leashed dogs are welcome, it’s best to leave pets at home because the crowds are usually pretty busy. Guests are encouraged to bring their own chairs to comfortably enjoy the live music, though coolers will not be permitted.

Eggstravaganza Egg Hunt (April 4, 2026, 10:00 AM–12:00 PM)

Head over to Centennial Park between 10 am and 11.30 am, to celebrate the Easter holidays with a festive Easter egg hunt suitable for children under 12 years old. Plus, from 11.30 am til 12 pm there’s a special Beeping Egg Hunt for blind and visually impaired children up to 16 years. 

The event features over 2000 thousand hidden eggs, face painting, and a special appearance by the Easter Bunny. It’s free to participate in the search, and a fun yet chilled way to celebrate the holiday with the community.​

6th Annual Spring Fling Skim Jam (April 25th – 26th, 2026)

Zap Skimboards host this ridiculously fun event which brings together professional and amateur skimboarders for a weekend of competition and camaraderie in Nokomis. 

Attendees can enjoy a free skim clinic, watch high-energy contests, and meet top athletes during autograph sessions. The beachside event also includes music, food vendors, and raffles.​

If you’re hoping to participate, be sure to register in advance as on-the-day entries will not be permitted. Otherwise, grab your towel and enjoy an action-packed day of watersport display at what is fast becoming one of the most fun Springtime events in Venice. 

33rd Annual Downtown Venice Craft Festival  (June 20-21, 2026)

This beloved annual event transforms the streets of Historic Downtown Venice into an outdoor gallery filled with handcrafted treasures. Discover an array of unique items including jewelry, pottery, woodworking, wearable art, home décor, and more—each created by talented artists and artisans from across the country. 

Admission is free, and there’s plenty of shaded sidewalk space for browsing comfortably. Parking is available in nearby lots and public garages. 

The event is presented by Howard Alan Events in collaboration with Venice MainStreet, making it the perfect weekend outing for art lovers and curious shoppers alike.

Wellen Park ® Events and Festivals

If you haven’t been to a Wellen Park event this spring, you’re definitely missing out! More than just a place to live, it’s a vibrant community hub where the lifestyle really shines. The downtown area is where it all comes to life—live music, outdoor markets, family-friendly festivals, and more.  Here are some of our top picks this season:

Family Fun Day (April 11, 2026)

Downtown Wellen Park comes alive with laughter and play at the annual Family Fun Day on April 12, 2025, from 12:00 PM to 4:00 PM. The event is free to attend, and packed with entertainment for kids and families. Some of the fun you’ll find includes carnival games, a bubbly foam party, colorful face painting, interactive arts and crafts stations, and more. 

It’s the perfect way to enjoy quality time outdoors with loved ones while soaking up the vibrant community spirit that defines Wellen Park. 

Country Music Festival (May 2, 2026)

If you’re looking for a fun, family-friendly night out this spring, the Country Music Festival at Downtown Wellen Park is one to add to your calendar. Happening on May 2nd from 4:00 PM to 10:00 PM, this lively event brings a little Southern charm to one of the area’s fastest-growing communities.

Be warned, this isn’t just a concert — it’s a full-on country-themed experience. You’ll find live performances from country artists, including rising talent like Derek Lersch and local favorites, along with line dancing, interactive activities, shopping vendors, and plenty of food options. The whole event is designed to feel like a relaxed, high-energy evening where you can wander, listen to music, and soak up the atmosphere.

The festival is free to attend, making it a great option for families, couples, or anyone wanting a laid-back night out without the ticket price. With its mix of live music, local vendors, and community vibe, it’s the kind of event that really shows off what makes the Venice and Wellen Park area such a fun place to live and visit.

Cars & Caffeine at Wellen Park® 

Start your morning in style at the Cars & Caffeine event hosted by the Venice FL AACA Car Club on the first Saturday of every month except July and August, from 7:30 AM to 10:00 AM, at Wellen Park Boulevard in Venice. 

This casual and welcoming gathering invites classic car lovers, exotic car enthusiasts, and curious onlookers alike to enjoy a stunning display of automobiles while sipping fresh coffee and chatting with fellow car buffs. The event is free and open to all ages. 

Nearby Events & Festivals in Southwest Florida

Spring is a fantastic time to explore Southwest Florida’s vibrant lineup of festivals and community events. From coastal food fests to art shows and waterfront concerts, there’s always something happening. If you’re looking for spring events in Sarasota, annual events in Tampa, or just fun family things to do in Florida (not Disney), check out our top picks for seasonal happenings just a short drive from Venice!

Events in Boca Raton:

Boca H2O Music Festival – May 23, 2026

Dive into two days of sunshine, music, and water fun at the Boca H2O Music Festival in Boca Raton. This high-energy beachside event brings together top DJs and live acts, setting the stage for an unforgettable party atmosphere. 

Expect everything from EDM to pop, immersive light shows, and interactive experiences like water slides, foam zones, and floating stages and lounges. The festival caters to both day-partiers and night owls with extended set times and VIP cabana options. 

This Boca Grand Sandbar event is free to attend, and parking is available nearby with both self-park and shuttle options, but attendees are encouraged to arrive early or use ride-sharing services for convenience.

Events in Bradenton:

De Soto Grand Parade  (April 25, 2026)

The De Soto Grand Parade returns, as one of the top things to do in Bradenton, on April 26, 2025, bringing vibrant energy and rich local tradition to the heart of Manatee Avenue. Hosted by the Hernando de Soto Historical Society, this lively celebration honors the Spanish explorer Hernando de Soto, whose 1539 landing near Shaw’s Point is central to local lore. 

The Grand Parade is the crown jewel of a month-long series of events and is considered one of the oldest and largest parades in the Southeast. Spectators line the streets to enjoy dazzling floats, costumed performers, and collect festive beads and trinkets tossed into the crowd. 

The event is free and family-friendly, drawing locals and visitors alike for a night of history, fun, and community spirit.

Spring Events in Sarasota:

Sarasota Film Festival 2025 (April 10 – 19, 2026)

Celebrating its 28th year, the Sarasota Film Festival is a premier event showcasing over 200 films, including features, documentaries, and shorts from both established and emerging filmmakers. 

Attendees can enjoy Q&A sessions, panel discussions, and special appearances by industry professionals. The festival also emphasizes educational programs and community outreach, making it a cornerstone of Sarasota‘s cultural calendar.​

To avoid paying higher ticket prices, patrons are encouraged to pre-book showings or purchase a SFF membership (with discounts available) through the box office. 

La Musica International Chamber Music Festival  (April 6–10, 2026)

Enjoy world-class performances at the La Musica International Chamber Music Festival, happening April 6–10, 2026, at the Sarasota Opera House. This annual festival is in it’s 40th season and brings together accomplished musicians from around the globe for a series of intimate concerts featuring classical masterworks and modern pieces. 

Guests can also attend rehearsals, lectures, and special events designed to deepen appreciation for chamber music. For performance schedules and ticket info, visit the official La Musica website. Parking is available in nearby public garages and street parking is accessible throughout downtown Sarasota.

Suncoast Boat Show (April 17 – 19, 2026)

The Suncoast Boat Show returns to Marina Jack in Sarasota, offering 65,000 square feet of dockside excitement from luxury motor yachts and sportfishers to kayaks and inflatables. 

It’s the perfect day out for all ages, especially with Captain Don’s Kids Fishing Clinics, where kids can learn fishing techniques and go home with a free rod and reel! 

In addition to boats, you can explore vendor tents filled with marine accessories, electronics, clothing, jewelry, and nautical art. Children 15 and under get in free, and active military and veterans enjoy complimentary admission with ID. There is no box office onsite so remember to purchase your digital tickets in advance!

The event has been a local favorite for over 40 years, and with a portion of the proceeds supporting Mote Marine Laboratory’s ocean conservation efforts, it’s easy to see why. We agree that it’s definitely up there on the list of things to do in Sarasota this season. 

Elizabeth Moore Sarasota Open (April 5–12, 2026)

Part of the ATP Challenger Tour, the Sarasota Open attracts professional tennis players from around the world. Held at the Sarasota Sports Club, the tournament offers fans the chance to see rising stars compete on Har-Tru clay courts. 

The venue provides excellent amenities, including a clubhouse and viewing areas.​ Kids under 12 are admitted to the grand stand for free but still require a ticket. With a weather forecast of sunny but cool, it’s set to be a fantastic weekend event! 

Sarasota International Dragon Boat Festival (April 18, 2026)

Get ready for a thrilling day on the water at the Sarasota Dragon Boat Festival at Nathan Benderson Park! This exciting Gulf Coast event welcomes both competitive and community teams to race on a 400-acre world-class lake. 

Whether you’re a seasoned paddler or brand new, there’s a place for you—including solo participants via the ‘Experience Dragon Boat’ programs.

Race categories include 200m, 500m, and a 2K pursuit, or if you enter as a community team it’s three laps of 500m. 

Between races, attendees can enjoy the Health & Wellness Village, family-friendly festival vibes, and thrilling views of the action. Admission for spectators is free and race entry fees vary by division. 

Whether you’re paddling or cheering from the sidelines, the festival offers a day of excitement, food vendors, and family-friendly activities in a picturesque setting.​ Learn more or register here. 

Siesta Con 2025 (May 9, 2026)

Sarasota’s premier comic convention returns with a celebration of pop culture, featuring comic artists, voice actors, and gaming tournaments. Highlights include the original Batmobile display, cosplay contests, and a vendor hall filled with collectibles and artwork. It’s a must-visit for fans of comics, games, and sci-fi.

Kids under 10 go free and general admission is $10. You can upgrade to the VIP experience for $50 which gets you access to exhibitors and artists, cosplay contests, preferred seating, photo opportunities and autographing, and a VIP gift bundle! 

5th Annual Downtown Sarasota Spring Craft Fair (May 2 – 3, 2026)

This charming art festival takes over Five Points Park in the heart of Sarasota, transforming the downtown area into a vibrant celebration of creativity. 

Featuring 100% handmade works by talented U.S. artists, it’s an ideal weekend outing for art lovers and gift hunters alike.

Explore a variety of treasures including jewelry, pottery, ceramics, paintings, clothing, and more. The festival also features a lively Green Market with plants, orchids, spices, and gourmet treats to tempt your senses. With prices ranging from $15 to $3,000, there’s something for every taste and budget.

Add in some sunshine and the scent of fresh kettle corn, and you’ve got the perfect spring day out.

95th Annual Sarasota Tarpon Tournament (May 9 – June 14, 2026)

Step into fishing history with the 96th Annual Suncoast Tarpon Tournament in Sarasota— the world’s oldest tarpon tournament. Running from May 9 to June 14, this iconic event offers weeks of exciting angling, camaraderie, and community support. 

For just $150 entry fee, anglers can compete in divisions like junior, ladies, fly, His & Hers, and most releases. Weekly winners and select divisions advance to a two-day Fish-Off to determine the overall champion, whose name is inscribed on the historic trophy. 

Tarpon, known for their epic battles and thrilling leaps, are a true test of skill. With proceeds supporting local charities, this tournament blends sport, tradition, and giving back—making it a standout experience on Florida’s Gulf Coast.

Savor Sarasota Restaurant Week (June 1–14, 2026)

Sarasota is well known for its huge selection of welcoming and delicious restaurants and breweries. Celebrate 20 tasty years of Savor Sarasota from June 1–20, 2025! Over 50 restaurants across Sarasota County—from Longboat Key to Englewood—will serve up specially curated multi-course menus. 

Enjoy lunch for just $25 and dinner for $45 per person. It’s the perfect time to explore new spots or revisit your favorites. With flavors from around the world, reservations are highly recommended for this foodie favorite!

SPRING EVENTS IN FORT MYERS:

Fort Myers BBQ Bands & Brew (March 28, 2026)

If you’re up for a lively day trip just south of Venice, the BBQ, Bands & Brew Festival in Fort Myers is a great way to spend a spring Saturday. Taking place on March 28th from 11:00 AM to 6:00 PM at the Caloosa Sound Amphitheater, this family-friendly event combines great food, live music, and a relaxed outdoor atmosphere.

Expect a mix of food trucks, games, and live entertainment, with headlining performances like Hair Daze bringing energy to the stage throughout the day. It’s designed to be a casual, come-and-go style event where you can grab some BBQ, enjoy the music, and soak up the waterfront setting.

Even better, the festival supports a good cause — with proceeds benefiting Lee BIA Builders Care, a local nonprofit that provides emergency home repairs for elderly and disabled residents. It’s a fun, feel-good event that mixes great local vibes with community impact.

Fringe Fort Myers (May 28 – 31, 2026)

If you’re looking for something a little different (in the best way), Fringe Fort Myers is one to keep on your radar this spring.

This isn’t your typical theatre event—it’s bold, a little quirky, and full of surprises. Fringe is an unjuried performing arts festival, which basically means anything goes. You’ll find a mix of local and traveling performers bringing everything from comedy and storytelling to music, dance, and completely unexpected acts to the stage.

The excitement starts building throughout March with teaser shows, special events, and sneak peeks, leading up to the full schedule reveal on March 31. Then, tickets officially go on sale April 1 (and yes, some of these shows can sell out, so it’s worth grabbing them early).

One of the coolest parts? Every ticket you buy goes straight to the performers, so you’re not just having a fun night out, you’re supporting real artists and the local creative scene.

India Fest at Fort Myers  (March 14th, 2026)

Immerse yourself in the vibrant colors, flavors, and rhythms of India at the annual India Fest in Fort Myers. This popular celebration of Indian culture features traditional dance performances, live music, and a wide array of Indian cuisine—from savory street food to rich, flavorful curries. 

Visitors can explore cultural exhibits, shop for handmade crafts and clothing, and watch stunning showcases of classical and Bollywood-style dance. The family-friendly event is in it’s 34th year and typically draws around 3000 attendees from across Southwest Florida. 

Grow Fort Myers & Orchid Symposium  (April 11 – 12, 2026)

Celebrate sustainability and nature at the Grow Fort Myers & Orchid Symposium, at the UF/IFAS Extension in Fort Myers. This two-day event blends eco-conscious gardening education with the beauty of orchids, offering workshops on native plants, composting, pollinators, and water-wise landscaping. 

Orchid lovers can attend special talks from experts and shop for unique plants and garden supplies. 

There will also be kids’ activities, food vendors, and opportunities to connect with local environmental organizations. Admission is free, but registration may be required for some workshops. 

Events and Festivals in St Pete, Florida: 

Tampa Bay Blues Festival (April 10 – 12, 2026)

Experience the soulful rhythms of the Tampa Bay Blues Festival at scenic Vinoy Park in downtown St. Petersburg. This waterfront festival features a stellar lineup including Kenny Wayne Shepherd, Taj Mahal & The Phantom Blues Band, Jimmy Vaughn, Los Lobos and more.  

Guests can enjoy local food vendors, craft beers, full bars, and wine while soaking in the music. Don’t miss the official Kick-Off Party at the Palladium Theater on April 10. 

Kids under 12 are free but all entrants must have a scannable ticket either printed or on your phone. Tickets start at $75, with the top VIP tier reaching $800. Parking is limited near Vinoy Park, so plan ahead and check nearby public lots or garages.

St. Pete Pride Festival  (June 26–28, 2026)

Celebrate love, diversity, and community all month long at the St. Pete Pride Festival, returning this June for its 24th year. Throughout the city of St. Petersburg, the festival will host events including concerts, parades, art shows, and community gatherings, with major highlights like the Friday Night Concert & Market,  Pride Parade and Festival on the Saturday, and the Sunday Street Fair. 

This iconic event draws thousands and supports the LGBTQ+ community and allies. For updates, schedules, and ticketed event info, visit the St. Pete Pride website. 

Events and Festivals in Tampa:

Keel Farms Blueberry Festival  (Every Sat & Sun in April 2025)

Nothing says spring better than the sweet taste of perfectly ripe blueberries. Keel Farms savor this time by hosting the annual Blueberry Festival in Plant City, with events running every Saturday and Sunday throughout April from 10 a.m. to 3 p.m. 

This free, family-friendly event features blueberry picking, a blueberry shortcake eating contest, and a host of farm activities including camel rides, bounce houses, and a petting zoo. Local vendors, food trucks, and Keel and Curley’s signature blueberry wines round out the experience. 

Admission is free, with parking available on-site for $10 per vehicle. It’s the perfect day out for families, foodies, and fans of Florida-grown produce.

Tampa Bay Wine & Food Festival (April 7 – 11, 2026)

The Tampa Bay Wine and Food Festival is a culinary celebration that brings together top chefs, winemakers, and spirits producers for five delicious days of tastings, dinners, and waterfront events. 

From curated wine pairings to signature tasting nights under the stars, this festival showcases the best of Tampa’s culinary scene. Proceeds benefit the Community Initiatives Foundation’s EAT SMART campaign, which supports youth wellness in the area. 

You’ll find organised events in Tampa and St. Petersburg, drawing a crowd of food lovers and industry insiders. For full schedules and tickets, visit the official festival website. 

Tampa Bay Black Heritage Music Festival (April 25–26, 2026)

Now in its 26th year, the Tampa Bay Black Heritage Music Festival returns to Curtis Hixon Waterfront Park for two days of soulful celebration. From noon to midnight each day, guests can enjoy an incredible mix of live performances by national and local Black artists across genres, along with food trucks, art vendors, and cultural exhibitions. The festival honors African American heritage through music, community, and education. Admission details and performance schedules will be available soon at tampablackheritage.org. Located in the heart of downtown Tampa, the venue is accessible via parking garages and public transportation.

Tampa Caribbean Carnival  (April 18 – 19, 2026)

The 21st Annual Tampa Caribbean Carnival is a joyful explosion of color, rhythm, and island spirit, held at Perry Harvey Sr. Park. Experience the vibrant parade featuring masqueraders in elaborate costumes dancing through the streets, then enjoy an evening of live Caribbean music with performers like Alison Hinds, Lyrikal, Mical Teja, and more. 

The park transforms into a cultural village with authentic Caribbean food vendors, arts, crafts, and family-friendly fun, as this is one of the biggest and most popular annual Tampa events. This celebration of Caribbean heritage is free for kids under 5 to attend, though various tiered admission and VIP options are available for youths and adults. Street and garage parking is available nearby, but carpooling or rideshares are recommended as it does draw quite a crowd. 

6th Annual Juneteenth Festival (June 15 – 20, 2026)

Presented by Roc the Block Inc., the 5th Annual Juneteenth Festival brings together the community for a powerful and joyful celebration of freedom and Black culture. 

Featuring live music, spoken word, dance performances, and family activities, this free event honors the legacy of Juneteenth and promotes education and unity. Guests can also explore local vendors, cultural food stalls, and historical exhibits. 

Various events, seminars, and performances will take place over the five days, ranging in price from free to $300. A full itinerary can be found here. 

Which Spring Events in Venice, Florida Will You Make It To?

From arts festivals to outdoor adventures and flavorful food events, spring in Venice and the surrounding Gulf Coast is full of excitement. It’s the perfect time to soak up sunshine, enjoy the warm breeze, and explore everything Southwest Florida has to offer. Whether you’re a visitor or a local, don’t miss your chance to celebrate the season in true Florida style!

We’d love to know which events made it on to your calendar. Share your photos from local Florida events on Facebook and tag us in them @ThatFloridaLife

The post Top Spring 2026 Festivals & Events in Venice Florida (including Wellen Park®) & Southwest Florida appeared first on That Florida Life.

Venice, Florida Events and Festivals

Regular and Recurring Events in Venice, Florida

Venice has an impressive list of things to do. In addition to the year-round options, the Venice, Florida, event calendar is vast and varied. The area has a massive selection of regular events scheduled daily, weekly, or monthly especially during the winter months (which is considered high-season here). No matter how you spend your ideal day, there is something for everyone to enjoy. 

• Venice Farmers Market

Held every Saturday morning in Venice City Hall, this market features fresh produce, handmade items, and live music. From 8 AM til 1 PM, you can soak up the lively community atmosphere of historic downtown Venice while filling up on seasonal and artisanal goods.  

• Movies in the Park

On January 16th and February 20th, Centennial Park hosts a movie night, offering free entertainment for all ages. Remember to bring your chairs! 

• Yoga On The Beach

Start your day right with an early morning yoga session on the pristine Gulf Coast sand. Every morning from 8 AM, and every evening from 5 PM, you can nourish your mind, body, and soul with some sun, sand, and stretching right here on Venice Beach! 

• Historic Venice Tours

Whether you want to tour Venice’s architecture, golf scene, wild women, or haunted history, you won’t be disappointed! Daily tours of historic downtown Venice are scheduled throughout the week/month.  

Major Events in Venice, Florida Winter 2026

In addition to the regular daily and weekly schedule, Venice has some more significant events that happen annually or even as a one-off. Some of our favorite holiday events are covered in the video below, and a deeper dive into the full winter schedule follows in the post below.

Wine & Chocolate Walk (February 12, 2026)

Indulge in a decadent evening exploring downtown Venice’s shops and restaurants, each offering unique wine and chocolate pairings. This beloved annual event is a favorite for couples and friends looking for a fun and flavorful night out. 

Guests can expect an evening filled with delicious flavors, lively conversation, and a warm, inviting atmosphere. Downtown Venice provides the perfect backdrop, with its twinkling lights, boutique storefronts, and welcoming restaurants creating a truly magical experience. Many businesses also offer special promotions and discounts, making this an excellent opportunity to shop locally while you sip and snack.

The event’s walkable nature ensures an easy and enjoyable experience, and it is also accessible for guests with mobility needs.

Online tickets will go on sale closer to the date, costing $10 each, and a limited number of tickets will be available for in-person purchase at the Information Kiosk in Centennial Park. Be sure to grab yours before they’re gone.

Exotic Race Car Event  (February 21, 2026)

Car enthusiasts and casual spectators alike won’t want to miss this once-in-a-lifetime automotive spectacle as the world-famous 1000 Miglia road race makes its way through Downtown Venice. This legendary 3-day, 1,000-mile journey takes drivers on an incredible route across Florida, from Miami to Naples, Cape Canaveral, West Palm Beach, and back to Miami, with Venice as one of its most exciting stops along the way.

Prepare to be amazed as over 70 vintage race cars and modern supercars cruise into Centennial Park, showcasing a dazzling lineup of rare, historic, and high-performance machines. The event is free and open to the public, making it an unmissable opportunity to witness some of the world’s most stunning and exclusive cars.

The festivities begin at 3 PM, when the Venice AACA Car Club kicks off the celebration with a display of classic and collector vehicles, offering a glimpse into automotive history. The 1000 Miglia race cars make their grand entrance between 4 and 5 PM. Be sure to arrive early, grab a great viewing spot, and be ready to capture an unforgettable moment in Venice’s automotive history!

Italian Feast and Carnival (February 19-22, 2026)

Get ready for a four-day celebration of all things Italian at the Annual Italian Festival hosted by the Italian American Club of Venice. This beloved tradition has brought the community together for an impressive 37 years, offering an authentic taste of Italy with delicious food, live entertainment, and family-friendly fun. At the Venice Airport Festival Grounds, the festival is a must-visit event for locals and visitors alike who want to experience Italian culture in a lively, welcoming atmosphere.

Of course, the highlight of the festival is the incredible Italian cuisine. Enjoy all your favorites, from freshly made pasta, meatball subs, and sausage and peppers to crispy cannoli, tagliatelle, and homemade Italian desserts. Pair your meal with a glass of fine Italian wine or a refreshing beer as you take in the sights and sounds of the festival.

Live music and entertainment will keep the energy high throughout the event, featuring a mix of traditional Italian performances and popular favorites. Dance along, sing with the crowd, or soak up the festive atmosphere. Kids and thrill-seekers will love the carnival rides and games, making this a perfect event for the whole family.

At just $5 per person, the festival is affordable and fun for all. Even better, kids under 10, active military, veterans, police officers, and firefighters get in free as a token of appreciation for their service.

Whether you’re craving authentic Italian flavors, looking for great entertainment, or want to enjoy a fun-filled weekend with friends and family, the Venice Italian Festival is the place to be. Come hungry, bring your dancing shoes, and celebrate Italian heritage in true Venetian style!

Venice Art Classic Festival (February 28 – March , 2026)

Enjoy a weekend of art, creativity, and community spirit at the Venice Art Classic Festival, where downtown Venice transforms into an open-air art gallery! Taking place Saturday, February 28, and Sunday, March 1, 2026, from 10 AM to 5 PM, this juried art festival brings together talented artists from across the country to showcase their finest work along West Venice Avenue.

Art lovers can browse and purchase a diverse selection of artwork, including captivating sculptures, striking paintings, intricate jewelry, hand-crafted ceramics, and more. Whether you’re a seasoned collector or just looking for the perfect statement piece for your home, this festival offers something for everyone.

Beyond the stunning artwork, this event is one of the most inspiring art festivals in southwest Florida. It’s also an excellent way to support the local community. Proceeds from the event benefit Venice MainStreet, a nonprofit dedicated to preserving and enhancing historic downtown Venice. By attending, you’re celebrating the arts and helping keep Venice’s cultural heart thriving.

As a free outdoor event, the festival is perfect for a leisurely day of strolling, shopping, and soaking in the artistic atmosphere. Parking is available in public lots and nearby street parking, but arriving early is recommended to secure a good spot.

Venice Sharks Tooth Festival (April 11-12, 2026)

Celebrate Venice’s reputation as the “Shark’s Tooth Capital of the World” at Centennial Park with fossil and beach-inspired merchandise vendors, live music, and delicious food. Although technically, it doesn’t take place until Spring, as it’s scheduled for April, it’s such a great event that we want to ensure you have plenty of notice to bookmark it in your calendar! 

Venice’s beaches are renowned for their abundance of fossilized shark teeth, which attract enthusiasts worldwide. The area’s unique geological history has resulted in a rich deposit of these fossils along its shores. You can check out some great fossil finds on our YouTube video here. 

This weekend-long family-friendly festival is free and packed with fun activities for all ages. Kids can enjoy the interactive shark-themed play area, which includes face painting, shark tooth hunting, and more. 

While leashed dogs are permitted at the festival, it is recommended that pets be left at home due to the expected crowds. Attendees are encouraged to bring their own chairs to enjoy the musical performances comfortably; however, coolers are not allowed.

Wellen Park® Events and Festivals

You’re missing out if you haven’t attended an event at Wellen Park yet! It’s not just a place to live—it’s a whole lifestyle. The downtown area is the heart of it all, with live music, markets, and fun events happening all the time. The downtown area is regularly alive with the Friday Night Concert Series, the ever-popular Wellen Night Market, and rotating live performances that turn an ordinary evening into a reason to hang out a little longer. On top of that, there are ongoing community offerings like toddler groups, theatre workshops, line dancing classes and other casual gatherings that make it feel easy to plug in whether you live nearby or are just visiting from a bit farther afield.

Luminescence Festival  (January 9, 2026)

This is one of those events that feels genuinely magical without trying too hard. Think glowing installations, artful lighting, and an evening atmosphere that’s perfect for wandering with friends or family. Set in Wellen Park’s town center, it’s a brand new event for the cooler winter months and is designed to be immersive rather than rushed. It runs from 5pm  onwards and is free to attend. The luminary bags are on a first come first served basis though so get there early to make sure you don’t miss out. Participants can personalize their luminary bags with New Year wishes or messages of rememberance, which adds a special intimate vibe to the event. Take part in the parade and release and then enjoy the live music, art, and fireworks.

Wellen Night Market  (2nd Thursday of every month)

If you love browsing handmade goods with a drink in hand, the Wellen Night Market is an easy favorite. Local makers, small businesses, and food vendors line the streets, often with live music adding to the vibe. It’s casual, social, and very much a “let’s just stroll and see what we find” kind of evening. These markets are usually free to attend, making them a low-key way to experience the community while supporting local creatives.

Wellen Park Fine Arts Festival (February 15th, 2026)

The Wellen Park Fine Arts Festival draws artists from across the region and turns the downtown area into an open-air gallery. You’ll find everything from paintings and photography to sculpture and functional art, all set against Wellen Park’s waterfront backdrop. Admission is typically free, making it a lovely daytime event to wander through, chat with artists, and maybe come home with something truly one-of-a-kind.

Half Marathon & 5K (March 21st, 2026)

Whether you’re running or cheering from the sidelines, the Wellen Park Half Marathon & 5K is a standout winter event. The course weaves through the community, showing off the scenery while keeping things festive. Registration fees vary by race and timing, but it’s well-organized and welcoming to runners of all levels. Even if racing isn’t your thing, it’s a fun morning to be out and about in Wellen Park, soaking up the energy.

Nearby Events & Festivals in Southwest Florida

Southwest Florida is the perfect place to experience vibrant events and festivals celebrating art, culture, and community. With its coastal charm and lively downtown hubs, the region sets the stage for everything from intimate local gatherings to major festivals that draw crowds from near and far. Whether you’re strolling through an art show, enjoying live music by the water, or indulging in a seasonal food festival, there’s no shortage of ways to get out, have fun, and soak up the sunshine. If you’re ready to explore beyond Venice, buckle up because you’re never far from an unforgettable event! Look at our top picks of what’s on offer this season from nearby areas in Southwest Florida. 

Fort Myers Beach – Shrimp Festival (March 7 – 8, 2026)

A much-loved Florida tradition celebrating the local shrimping industry, the Fort Myers Beach Lions Club Shrimp Festival is the premier annual Fort Myers event. The pre-festival activities kick off on March 1 with a kids’ shrimp run, and the full festival schedule commences March 7-8, 2026, at Lynn Hall Memorial Park. The festival features a parade, arts and crafts fair, Queens Pageant, and a shrimp-eating contest. 

Parking is available at North Beach Park Plaza, offering over 600 spaces at $3 per hour. Additionally, the LeeTran trolley service is a regular public transport option. 

The best thing about this event is that while it’s free to attend, the festival is a huge fundraising event for local charitable initiatives. Proceeds from the event support everything from local eye surgeries and vision care to scholarships for students and programs like Southeastern Guide Dogs. It also helps fund youth sports, large-print books for the library, and essential resources for local schools. 

So, while you’re enjoying a plate of fresh “Pink Gold” shrimp and checking out the parade or craft fair, you’re also helping support amazing causes that directly benefit the area. It’s a win-win—good food, good times, and giving back!

Sarasota Winefest (March 21, 2026)

Mark your calendar for the Sarasota Wine Festival on Saturday, March 21, 2026, at Selby Five Points Park in Downtown Sarasota! Enjoy an unforgettable evening filled with world-class wines, craft cocktails, gourmet food trucks, live music, and unique lifestyle vendors.

General Admission (6–9 PM) includes unlimited wine tastings, a souvenir wine glass and tote bag, a food truck voucher, craft cocktail samples, and access to a pop-up wine shop.

VIP Admission (5–9 PM) includes everything in General Admission plus early entry, a private lounge with seating, exclusive wine selections, sommelier access, private bathrooms, heavy hors d’oeuvres, and a VIP swag bag. Limited VIP tickets are available!

Admission to the festival is free, so you can enjoy live music and browse vendors. Still, tasting tickets are required to indulge in wine and spirits, and will go on sale from February 1st. This year’s festival supports the Women’s Resource Center, a nonprofit helping women in Sarasota and Manatee Counties through education, career guidance, wellness programs, and more. Plus, the event will spotlight local women entrepreneurs and businesses. So gather your friends, sip, shop, and savor an incredible night—all for a great cause! 

Sarasota Jazz Festival (March 9-14, 2026)

Tickets are on sale now for the 46th annual Jazz Festival, which will take place March 9-14 at various venues throughout Sarasota. Music lovers can enjoy a week of this fantastic festival, which offers world-class cabaret performances and lively jazz trolley pub crawls. Tickets are sold individually for each event so that you can curate your perfect jazz experience. Food and drinks will be available at all venues. 

Jazz enthusiasts can upgrade to a VIP Experience, which includes priority seating at all main stage performances, entry to the Monday Night Jazz Cabaret, access to the Jazz Trolley Pub Crawl, and an exclusive VIP Reception on March 17 featuring a special performance by Danny Spinoff at the John C. Court Cabaret, Florida Studio Theatre. 

Don’t miss this jazz celebration in the heart of Sarasota—secure your tickets here!

St Petersburg Firestone Grand Prix (Feb 27 – March 1 2026)

The Firestone Grand Prix of St. Petersburg, presented by RP Funding, will ignite the streets of downtown St. Petersburg from February 27 to March 1, 2026. This thrilling event features a 1.8-mile, 14-turn temporary circuit that winds through iconic landmarks such as Pioneer Park, the Duke Energy Center for the Arts, and The Dalí Museum. It even incorporates sections of the Albert Whitted Airport runway, all against the stunning backdrop of Tampa Bay.

Beyond the high-speed racing action, attendees can look forward to a festival-like atmosphere featuring speed zones, an IndyCar Series Fan Village, beer gardens, driver autograph sessions, and interactive games and exhibits. 

Parking is available at several downtown garages, including the SouthCore Garage, Sundial Garage, and the University of South Florida (USF) Garage. Additional parking can be found at Tropicana Field, with a free shuttle service running to and from the race venue. Accessible parking is available on a first-come, first-served basis, and fans are encouraged to use public transportation or ride-sharing services for easier access.

Tickets start at $25 for a single day and go up to three-day general admission, priced at $75 for adults and $65 for children 12 and under. There’s also an option for three-day grandstand seats, which offer reserved seating with excellent views for just $135. You can purchase tickets here.

Florida Strawberry Festival (February 26 – March 8, 2026)

The Florida Strawberry Festival has been a cherished tradition since 1930, celebrating its 91st annual event in 2026. It’s one of the most popular events in the state, attracting over 600,000 visitors each year.  This annual celebration honors the region’s rich strawberry harvest with entertainment, agriculture, and family-friendly activities. It runs from February 26 to March 8, 2026, in Plant City, Florida. 

Attendees can explore displays showcasing local agriculture, including youth livestock shows and the Neighborhood Village, which features homemade crafts and goods. For thrill-seekers, the festival offers a variety of rides and games suitable for all ages. Not least, foodies can indulge in many strawberry-themed treats, from the classic strawberry shortcake to innovative culinary creations.

The festival also boasts an impressive lineup of headline performers. Tickets for these concerts are sold separately and can be purchased here.

On-site parking is available for attendees. It’s advisable to arrive early, especially on weekends, to secure a convenient spot.

Advance tickets are $10 for adults and $4 for children aged 6 to 12. Tickets at the gate are $15 for adults and $5 for children. Children 5 and under enjoy free entry.

Island Fest (March 28-29, 2026)

Get ready for a weekend of island vibes, art, music, and coastal fun at one of the best beach festivals in Florida! The 34th Annual Island Fest in Islamorada will be held March 28-29, 2026, at Founders Park (MM 87 Bayside). The festival is a free, family-friendly event that brings together the best of the Keys—live music, delicious food, stunning art, classic cars, and exciting competitions.

One of the highlights of Island Fest is the Plantation Yacht Harbor Arts & Crafts Show, featuring over 100 talented artists showcasing everything from paintings and sculptures to handmade jewelry and driftwood carvings. Music lovers can enjoy live performances all weekend, adding to the fun, laid-back island atmosphere. There’s also a Classic Car Show, where beautifully restored vintage automobiles will be displayed.

For families, there’s plenty to keep kids entertained, from hula hoop contests and kite flying to an epic sandcastle-building challenge. One of the most unique events of the festival is the “What Floats Your Boat?” homemade boat race, where teams construct their vessels and compete for fun and quirky awards, including the Lucky Ducky Admiral Award. The excitement continues with the Sand Sculpture Competition, where teams create stunning masterpieces inspired by this year’s theme, “Ocean Wonders.”

No festival is complete without fantastic food, and Island Fest delivers! Savor fresh seafood, tropical island flavors, and classic festival bites while enjoying the ocean breeze. Various vendors will offer everything from conch fritters to refreshing tropical drinks on-site.

Best of all, admission to Island Fest is entirely FREE! On-site parking is available for a $10 donation, and festival hours are 10 AM—5 PM both days. Bring your lawn chairs and blankets to stay comfortable and enjoy the festivities. In an effort to keep the scene green, attendees are encouraged to bring reusable drink containers to help reduce waste.

Don’t Miss Out on these Popular WinterVenice, Florida Events (and Nearby Areas)!

With so many exciting events in Venice, Florida, and some of the best festivals in Florida, there’s no shortage of fun this season! Mark your calendars, grab your tickets, and experience the vibrant culture, stunning coastal scenery, and community spirit that make Southwest Florida an incredible place to live and visit!

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