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Can’t-Miss St. Pete / Clearwater Fall Events & Festivals

As the vibrant hues of autumn foliage begin to paint the landscape, St. Pete and Clearwater come alive with a cornucopia of fall festivals and events that capture the essence of the season. From thrilling powerboat races to sizzling chili festivals and elegant art showcases, there's something for everyone to enjoy in our captivating coastal paradise. Read on to discover the most anticipated fall happenings for Clearwater / St. Pete in autumn.

Big-League Sports (Seasonal)

Local sports fans have always had lots to get excited about once the fall season rolls around. The mighty Tampa Bay Buccaneers kick off their season at home with a matchup against the Chicago Bears at Raymond James Stadium on Sept. 17. The NHL’s Tampa Bay Lightning hit the home ice beginning with an exhibition game vs. the Carolina Hurricanes at Amalie Arena on 9/29. Baseball fans still have lots of opportunities to catch a Tampa Bay Rays home outing at Tropicana Field through the end of the regular season. Plus — the USL’s Tampa Bay Rowdies still have plenty of home games on the schedule at Al Lang Stadium well into October. So grab a seat, and root for the hometown heroes!  

St. Pete Powerboat Grand Prix (Sept. 1 – 3)

Kick off your fall festival journey with a roar as the St. Pete Powerboat Grand Prix takes center stage over Labor Day Weekend. This high-octane annual event transforms the picturesque waterfront into a thrilling racecourse for the world’s most horsepower-heavy powerboats. Feel the adrenaline rush as these sleek vessels speed across the waters of Tampa Bay, captivating both boating enthusiasts and curious onlookers alike. The event not only showcases incredible maritime skills but also raises funds for local charities, creating a sense of community and camaraderie.

St. Pete Pier, 600 2nd Ave NE, St. Petersburg, FL 33701

Bucs Beach Bash (Sept 8 – 10)

Sports fanatics and beachgoers join forces at the Bucs Beach Bash, a dynamic event that combines the excitement of football with the laid-back beach culture. Held right on-site at RumFish Beach Resort (and in partnership with the Tampa Bay Buccaneers), this fantastic festival offers a unique blend of live music, beach games, autograph sessions with players, and exclusive fan experiences. So don your team colors, soak up some sun, and revel in the energy of your fellow fans as you celebrate the spirit of the sport and the community. Best of all? Admission is FREE!

RumFish Resort, 6000 Gulf Blvd, St Pete Beach, FL 33706

I Like it HOT! Festival (Sept. 11 – 12)

I Like it HOT! is the largest hot sauce festival in the Sunshine State, and a must-attend celebration for those who savor the spicier side of life. This fiery extravaganza brings together chili lovers from all around the world to indulge in a variety of hot sauces, salsas, and other tongue-tingling creations. Sample the heat from a variety of vendors and witness hot sauce competitions that will test even the most daring of taste buds. With live music and an upbeat atmosphere, this bash is a sensory delight that promises a memorable culinary adventure. Parking and admission are FREE! 

Largo Event Center, 6340 126th Ave North Largo, FL 

St. Pete Art & Fashion Week (Sept. 15 – 16)

Fall is a season of transformation, and the St. Pete Art & Fashion Week beautifully captures this theme through the creative expressions of local artists and designers. Immerse yourself in a world of stunning visuals as galleries and runways showcase innovative artworks and fashion-forward designs. From elegant couture to thought-provoking installations, this event is a testament to the thriving art and fashion scene in the area, inviting visitors to appreciate the intersection of culture and aesthetics.

Various Locations — Click Here for more information

Clearwater Offshore Nationals (Sept. 22 – 24)

Calling all adrenaline junkies and boating enthusiasts! The Clearwater Offshore Nationals is an electrifying event that showcases some of the fastest and most powerful boats as they compete in heart-pounding offshore races. Feel the thrill as these watercrafts push the limits, creating a rip-roaring, breathtaking spectacle that will leave you on the edge of your seat. Whether you're a seasoned boater, or just can’t get enough of these surf-skimming skiffs, this event is a true testament to the region's affinity for all things nautical.

Pier 60, 7 Causeway Blvd. Clearwater Beach, FL 33767

St. Pete Pier Fall Festival (Oct. 7 – 8)

As the sun sets earlier and the air gets crisp, the St. Pete Pier Fall Festival beckons families and friends to come together and celebrate the changing of the seasons. This charming event offers a delightful blend of fall-themed activities, including pumpkin decorating, hay rides, live music, and local food vendors. Stroll along the newly revitalized St. Pete Pier, taking in the breathtaking waterfront views while indulging in classic fall treats and making cherished memories.

St. Pete Pier, 600 2nd Ave NE, St. Petersburg, FL 33701

Clearwater Jazz Holiday (Oct. 19 – 22)

For lovers of smooth melodies and rhythmic beats, the Clearwater Jazz Holiday is a musical journey that shouldn't be missed. Set against the backdrop of the tranquil Clearwater Harbor, this iconic event brings world-class performers to the stage, captivating audiences with their soulful tunes. This year, attendees will be able to catch legendary, household-name acts like The Beach Boys, Trampled by Turtles, Los Lobos, Gladys Knight, Buddy Guy and Kenny Wayne Shepherd. So spread out your blanket on the grass, bask in the warm fall breeze, and let the music transport you to a realm of relaxation and inspiration.

The Sound at Coachman Park, 255 Drew St, Clearwater, FL 33755

Shopapalooza Festival (Nov. 25 – 26)

As the holiday season approaches, the Shopapalooza Festival provides the perfect opportunity to discover unique gifts and support local businesses. This vibrant bazaar-style market showcases a diverse array of vendors offering handmade crafts, artisanal products, and delicious treats. It's a shopping experience that goes beyond the ordinary, allowing you to connect with the makers and creators behind the goods while enjoying a festive atmosphere that ignites the holiday spirit.

Vinoy Park, 701 Bayshore Drive NE, St. Petersburg, FL 33701

TradeWinds is the Perfect Stay for Autumn’s Events

With fall festivals and events that cater to a wide range of interests, St. Pete / Clearwater is a captivating destination for seasonal celebrations of all varieties. Whether you're a thrill-seeker, a foodie, an art enthusiast, or simply looking to bask in the beauty of the changing season, TradeWinds Resort is the ideal spot to call home during your visit. Our pair of resorts offer unbeatable comfort, convenience, and an on-site range of activities and amenities that are second-to-none. Check out our Special Offers page for all the best St. Pete Beach travel deals, and book your “just let go” getaway today!


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