Labor Day Weekend hangouts around Pinellas

in The Bay and the 'Burg/Top Headlines by

Whether you’re mingling this weekend to celebrate the end of summer, the start of football season, or the thrill of being alive, the Labor Day festivities in Pinellas County are here and ready to go.


OLDSMAR — Check out some fireworks and live music at Celebrate Oldsmar! The event’s being held both Friday and Saturday night, with the U.S. Stones set to take the stage day one, and The Super Stars day two. But the after-dark firework show is only scheduled for Saturday.

There will also be also carnival rides, live music, food, beer, wine, and games on both nights.

From 6 p.m. to 10 p.m. Friday (Sept. 4 ) and Saturday (Sept. 5) at R.E. Olds Park, 107 Shore Drive W.

For information about Celebrate Oldsmar!, go to

DUNEDIN — Hit up a free concert at Dunedin’s Highlander Park. The Shakes Society, whose repertoire includes rock, jazz, alternative music and more, will be the featured band. The event is part of Dunedin’s acclaimed Starlight Concert series.

From 7 p.m. to 9 p.m. Friday (Sept. 4) at Highlander Park, 1920 Pinehurst Road.

For more information call Highlander Park at 727-812-4530.

GULFPORT — The big-little city of Gulfport will be offering the complete package this Saturday — the event: Gecko Fest, an all-day block party with live music on two stages, hundreds of food, art and craft vendors, kids’ activities, and up-close and personal street performances by a slew of acrobats, magicians, daredevils, dancers, aerialists, escape artists, fire eaters, balloon artists and costumed characters.

From 10 a.m. to 10 p.m. on Saturday (Sept. 5), along Beach and Shore Boulevards in the heart of Gulfport.

For more, visit

ST. PETERSBURG — Maybe you’re in the mood for something a little smoother, with a little more air-conditioning. Then see what’s up with Keith Sweat at The Mahaffey Theatre this Saturday night. Sweat’s resume includes six chart-topping R&B singles and six multi-platinum albums. His debut album Make it Last Forever sold four million copies.

Show starts at 8 p.m. on Saturday (Sept. 5) at The Mahaffey Theatre, 400 1st St. S.

Visit for ticket prices and more.

CLEARWATER — Maybe dive into the local art scene a little this holiday weekend. The Osceola Gallery, at Clearwater’s Public Library, is showing “Love Affair with Cuba,” a photography exhibit inspired by the photographer’s (Leslie Joy Ickowitz) recent visit to Cuba. The exhibit opens on Saturday, Sept. 5, and runs through Sept. 25.

All day Saturday (Sept. 5) at Clearwater’s Public Library, 100 N Osceola Ave.

For more information, visit

ST. PETERSBURG — Perhaps you’re looking to get a little boozy this holiday weekend. If so, why not check out MacDinton’s Sunday Labor Day celebration. Party starts at 11 a.m., with live music bumping at 3 p.m. — sounds by Brandon Santino. They’ll also have a bunch of drink deals running all day, like $4 Mimosas and $5 Bloody Marys until 5 p.m.

From 11 a.m. to 3 a.m. on Sunday (Sept. 6) at MacDinton’s in St. Pete, 242 1st Avenue North.

For more information, click here:

ST. PETERSBURG — On the first Friday of every month, the beating heart of downtown St. Pete becomes Pinellas’ biggest block party, and this Friday is no exception. Start off your Labor Day weekend here if you’re in the mood for a showcasing of great bands, great drinks, great food and phenomenal people watching.

From 5:30 p.m. to 10 p.m. on Friday (Sept. 4), on Central Avenue, between 2nd and 3rd Street.

For more information, visit

ST. PETERSBURG — Let’s get a little cliche here — we “saved the best for last.” Behold, the free-floating Labor Day weekend sandbar concert. You’ll need a boat to get to it, but over the past eight years, this party has turned into one of the bay area’s most epic Labor Day bashes. The shindig basically just floats on a pontoon out in the middle of St. Petersburg’s Riviera Bay. Music will include some blues, some classic rock, and a master slide guitar player. The Cross Creek Blues Band puts on the party every year. Prepare for beer drinking and wading in waist deep water if you attend.

From 12 p.m. to 5 p.m. on Sunday (Sept. 6) in St. Petersburg’s Riviera Bay, in the “P” Channel, near Weedon Island.

For the complete scoop, visit

Devon Crumpacker is a Tampa Bay based writer and reporter for Extensive Enterprises Media. He primarily covers Pinellas County politics for, but also makes time to write the occasional bar review for He lives in St. Petersburg with his fiance, Sydney. To contact, e-mail [email protected], or visit his Twitter page @DevonCrumpacker.