#1 St. Pete Pride Kickoff Weekend
Celebrate the start of PRIDE season with St. Pete Pride this weekend across St. Petersburg. St. Pete PRIDE kicks off Friday night in the Grand Central District with a street fair, rolls into Saturday with a pickleball tournament and Sunday with a lively Drag Brunch then continues all of June. It’s the opening to a full month of events—one of the largest Pride celebrations in the Southeast—featuring everything from Family Day at the Pier to the iconic Pride Weekend and TransMarch & Festival.
See their full PRIDE calendar at https://www.stpetepride.org/2026-events.
#2 Rays Postgame Concert
Head to The Trop this Saturday, May 30th as the Tampa Bay Rays take on the Los Angeles Angels, then stick around for a postgame concert by Cole Swindell. With a string of Platinum hits and 13 No. 1 songs, the award-winning country star brings big energy to cap off a great night of baseball. It’s the perfect combo of America’s pastime and live music—just make sure you stay through the final out!
Get tickets at https://www.mlb.com/rays/tickets/postgame-concerts.
#3 Gulfport Pride Parade
Wrap up the weekend with one of Tampa Bay’s most heartfelt & vibrant PRIDE celebrations at the Gulfport Pride Parade on Sunday, May 31st 11am. This colorful community tradition marches through the Downtown Waterfront District, bringing neighbors, allies, and visitors together in a joyful show of love and inclusivity. The celebration concludes with a meaningful Pride flag raising ceremony—making it the perfect blend of festivity and purpose. Come out, show your colors, and be part of Gulfport’s joyful PRIDE.
Learn more at https://gulfportprideflorida.com/.
#4 Dunedin Pride Family Day
Celebrate a new chapter for Dunedin Pride Inc. this Sunday, May 31 with Family Pride Day in the Park. This kickoff event marks the organization’s exciting transition into an independent nonprofit—bringing even more inclusive, community-driven programming to Dunedin and beyond. Expect a joyful, welcoming atmosphere filled with connection, celebration, and Pride for all ages. It’s the perfect way to come together to be part of a growing tradition rooted in love, visibility, and community.
Learn more at https://www.dunedinpride.com/
#5 Underground Book Fair
Calling all book lovers, vinyl diggers, and curious minds—this one’s for you. The Underground Book Fair takes over The Jack Kerouac House this Saturday, May 30st with an eclectic mix of booksellers, record dealers, authors, and live readings in a laid-back, creative setting. It’s part literary gathering, part local marketplace, and all-around inspiring—perfect for discovering something new (or your next good read). Your $5 suggested donation supports a beloved local nonprofit.