What's Up in Florida
in May and June, 2026

MAY

HANG 8 DOG SURFING — Experience dog surfing competitions, a "Surfing Village" with vendors, and a doggie costume contest and a kissing booth. This community event supports local animal rescues and features dog surfing heats throughout the day.
When: May 31
Where: Daytona Beach/Flagler Beach area, near South 5th St. in Flagler Beach
Web: https://www.visitflagler.com/blog/post/watch-rover-ride-the-waves-at-the-hang-8-dog-surfing-competition-in-flagler-beach/

JACKSONVILLE JAZZ FESTIVAL — From the iconic echoes of Parliament Funkadelic featuring George Clinton to the modern soul of Andra Day, the Jacksonville’s annual jazz fest transforms the city into a vibrant, open-air celebration of music — both past and present. This year’s other headliners include Nile Rodgers and Chic, Galactic featuring Jelly Joseph, Moonchild and Ghost-Note. The main stage turns up the heat on Saturday with an all-star, female-led lineup with Esperanza Spalding, Sheila E., and more joining Day. Thursday’s Jazz Piano competition, held at the Florida Theatre, always kicks off the event with five finalists competing for $8,000 in prize money with the winner receiving a chance to perform on the main stages on Sunday. All concerts are free to the public, VIP ticket packages are available.
When: May 21-24
Where: Jacksonville
Web: https://jacksonvillejazzfest.com

GREAT AMERICAN BEACH PARTY – Celebrate with family and friends as a part of Fort Lauderdale Beach is transformed into an entertainment mecca. There are highlights galore: live music, water slides, a classic car show, SOCOM Para-Commando parachute jumpers, vendors, exhibitors, an art show, a sand-sculpting contest, a kids zone, a military tribute and the Walk of Fame ceremony
When: May 23
Where: Las Olas Oceanside Park, Fort Lauderdale
Web: fortlauderdale.gov/ and search for Great American Beach Party

JUNE

PANHANDLE WATERMELON FESTIVAL — Country music always takes center stage in Chipley when Tracy Byrd and Grace and Grit headline Chipley’s annual fest — a local staple that’s been rocking the heart of Florida since 1969. From the sunrise pancake breakfast to sunset performances, small-town spirit shines during this free weekend that also includes a car show, watermelon auction, parade and the Hot Trot 5K. Tracy Byrd, Dailey & Vincent and Ashley Monroe also will take the stage.
When: June 26-27
Where: Chipley
Web: https://www.panhandlewatermelon.com

JAX BEACH COUNTRY FEST — There’s no better way to kick off the summer beach season than with salt air, cold drinks, and the opportunity to catch rising stars in country music performing live at the oceanfront Seawalk Pavilion. Florida native Ashley Cooke (Never Til Now) headlines this year’s event. She’ll be joined by Preston Cooper, a country-rock artist known as the “Singing Mailman”, and Panacea, Florida, native Madden Metcalf, who’s new album, Saltwater Southern, just dropped. Rounding out the lineup is Fuller, Maurice, Steven Quinn and Liz Bechtle. The family-friendly music fest is free.
When: June 13
Where: SeaWalk Pavilion, Jacksonville Beach
Web: https://jaxbeachcountryfest.net

BROOKSVILLE’S WATERMELON FESTIVAL – What better way to ring in the summer than with this Central Florida fest featuring local-grown, cool, crisp watermelon? Batten Family Farms will roll out its prized fresh melons alongside vendors and food trucks selling lemonade, fair foods and other refreshments for sale. Enter a watermelon-eating contest or the kids’ pageant, meet some crowned members of “watermelon royalty,” and check out the local craft vendors to take home some handmade goods. Entry into the event is free, parking is ample and pets are welcome.
When: June 13
Where: Florida Classic Park, Brooksville
Web: https://www.facebook.com/events/s/brooksvilles-watermelon-festiv/966757305935078/

SARASOTA MUSIC FESTIVAL – Celebrating more than six decades of bringing top talent to central Florida, the Sarasota Music Festival is once again hosting several days of internationally recognized musicians in what’s considered one of the finest classical-music events in the nation. Enjoy a rare glimpse of both treasured top artists and young rising stars rehearsing and playing together, as well as hearing lectures and learning more about orchestra life and the role of each musician and instrument. In recent years, this event has infused some fresh sounds, breaking boundaries with jazz and bluegrass influences, and now offers a “flex pass” for those who want to enjoy more than one performance.
When: Several dates between June 1-June 13
Where: Sarasota Opera House and Beatrice Friedman Symphony Center, Sarasota
Web: https://www.sarasotaorchestra.org/festival

ANIME FESTIVAL ORLANDO – Celebrating an appreciation of Japanese culture within the anime and video game fan communities of Orlando, this three-day festival has grown over the past 25 years with its popular cosplay contests, video and tabletop game rooms, art and collectible galleries, and other activities geared toward this niche crowd. Play the interactive and exciting “Tales of Orlandia” game, exclusive to the event, and meet a variety of anime voice actors, famous cosplay artists and other special guests. There will also be several panel discussions, an origami workshop, a dance contest, crafting classes and other fun activities around the clock.
When: June 19-21
Where: Rosen Plaza, Orlando
Web: https://animefestivalorlando.com/

THE PINK RETREAT – Ladies of all ages, this one’s for you. It was created for folks of the fairer sex who love a colorful closet and want to enjoy an inspiring and welcoming weekend together and make new friends or continue bonding with old ones. Many of the activities are included with registration fee. Here’s what’s on tap: the opening day party, Poisoned in Pink: a murder mystery dinner, a one-hour eBike ride that tours Palm Beach’s coastal views, mixed-media art classes, cocktail classes, perfume classes, cooking classes, an evening of wine and culinary delights, the always-popular Pajamas Lounge, afternoon teas, luncheons with croquet lessons, trolley tours and the final-day farewell gathering.
When: June 11-14
Where: Various locations in Palm Beach County
Web: thepinkretreat.com/