Tampa Bay area residents are fortunate to have a plethora of year-round entertainment options, ranging from festivals and theatrical performances to sporting activities and world-class concerts. To assist you in planning ahead, we’ve curated a selection of activities scheduled from now through October 2026.
With holiday extravaganzas, annual festivals and chart-topping artists performing at venues nearby, you will discover numerous lively diversions to captivate you both this year and the next.
MLK Dream Big Weekend: Dr. Martin Luther King, Jr. Parade
TBD
St. Petersburg – Travels East to West on 1st Avenue South
This vibrant and inspiring parade winds through the heart of Downtown St. Petersburg along 1st Avenue South, ending at Tropicana Field. Celebrate the legacy of Dr. Martin Luther King Jr. and experience a dazzling showcase of floats from local organizations.
Raise the sails and get ready to catch plenty of beads during the annual Gasparilla Pirate Fest. Events include the Gasparilla invasion, Parade of Pirates and Pirate Fest.
Marc Dahl Studios (Courtesy of Gasparilla Festival of the Arts)
Gasparilla Festival of the Arts February 28 – March 1, 2026 Julian B. Lane Riverfront Park
Recognized as one of the top-rated outdoor fine art festivals in the country, this annual event welcomes more than 30,000 attendees. Beyond the art, the event offers something for everyone, from live music and culinary delights to family- friendly areas and activities for children.
River O’ Green Fest is a free annual event celebrating St. Patrick’s Day by turning the Hillsborough River a vibrant shade of green. Enjoy live Irish entertainment, food and drink vendors, beer, and fun activities for the whole family.
Sugar Sand Festival (Courtesy of Visit St. Pete-Clearwater)
Pier 60 Sugar Sand Festival March 27 – April 12, 2026 Clearwater Beach
Explore the expansive 24,000-square-foot structure that encompasses the Sugar Sand Walk Exhibit where sixteen professional sand sculptors transform sugar sand into breathtaking sculptures.
Tampa Bay Wine & Food Festival April 7 – April 11, 2026
This destination event will feature a variety of experiences that will bring together national wine and spirits producers and brands curated to highlight and celebrate the remarkable culinary abilities throughout the Tampa Bay area.
This annual event has become one of Tampa Bay’s largest celebrations of Latin flavors, showcasing over 100 empanada varieties from 25+ vendors, along with craft cocktails, live music and vibrant cultural entertainment. tampaempanadas.com
Bern’s Winefest (Courtesy of Pezz Photos)
Bern’s Winefest TBD
Presented by Bern’s Steak House, Haven, and Bern’s Fine Wines and Spirits, this annual event spans an entire week, offering the chance to indulge in your wildest culinary and wine fantasies.
The festival spans the entire length of the Riverwalk including several parks and features family-friendly activities and events showcasing Tampa’s cultural institutions, local musicians and restaurants.
St. Petersburg Pride stands as Florida’s largest Pride celebration, celebrated for its vibrant parade, lively festival, and welcoming atmosphere. The parade showcases vibrant floats, lively marching bands, and hundreds of participants, celebrating unity and pride within the LGBTQ+ community. The festival presents a diverse array of food, beverages, music, and entertainment choices for guests of every age.
813 Day at Hyde Park Village August 13, 2026 Hyde Park Village
Hyde Park Village will celebrate Tampa’s unofficial hometown holiday, 813 Day, with wellness events benefiting local charities, exclusive shopping and dining deals, family activities, and community programs.
FitFest Tampa Bay August 15 & August 16, 2026 Florida State Fairgrounds
FitFest, formerly the Tampa Bay Strength and Fitness Expo, is now Florida’s largest sports festival and fitness expo. This premier event brings together athletes, enthusiasts and industry professionals to celebrate strength, endurance and innovation.
Enjoy a themed casino night—all in support of making art accessible to everyone in our community. Try your luck at roulette, craps, blackjack, and more, knowing every dollar raised benefits the Tampa Museum of Art’s dynamic art education initiatives
Tampa Pig Jig October 16, 2026
Julian B. Lane Park
Each fall, the Tampa Pig Jig brings incredible live music, delicious food, ice-cold beer and a fierce corporate barbecue competition to downtown Tampa’s waterfront.
SAVOR St. Pete (Photography Courtesy of Melissa Santell, FoodxFeels)
Savor St. Pete November 1 – November 2, 2025 Vinoy Park
A culinary celebration featuring bites, wines, brews and spirits. Enjoy unlimited tastings from more than 100 brands, appearances by Food Network chefs Brian Malarkey and Carlos Anthony, live demonstrations and more.
St. Pete Run Fest November 14-16, 2025
Albert Whitted Park
Nationally recognized as one of the best running events of the decade, St. Pete Run Fest includes a half marathon, 10K, 5K, kid’s youth run and VEG PeliPAWS Dog Walk.
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