What's Up in Florida
in August and September, 2026

AUGUST

WAUSAU POSSUM FESTIVAL — Looking for a truly unforgettable Florida road trip? Head to the central Panhandle for Wausau’s annual Possum Fest! As the self-proclaimed Possum Capital of the World, this tiny town throws a massive party featuring a Possum Parade, live music, a quilt auction and hilariously authentic Hog Callin' and Rooster Crowin' contests. Be sure to dress the part (possum attire is highly celebrated) and don't skip out on the famous Possum Ice Cream. Don't worry, no possums were harmed to make it, instead it’s just a delicious blend that includes persimmon, the sweet and bitter fruit that the marsupials love.
When: July 31 - Aug. 1
Where: Wausau
Web: https://visitwcfla.com/events/wausau-possum-festival

BEERTOPIA – This evening event brings beer lovers, bands and local restaurants together in one fairgrounds hall, raising money for a nonprofit that supplies vision care and eyeglasses to children and the Hernando De Soto Historical Society. Enjoy samplings of various craft brews, seltzers and liquor, as well as live music, fun silent and live auctions, a raffle, and food made by some of the area’s most loved restaurants.
When: Aug, 22
Where: Manatee Couty Fairgrounds, Palmetto
Web: https://desotohq.com/beertopia/

DYNOMITE DUO FOR FOODIES! – You can eat your way through Miami-Dade and Broward Counties at some of SoFla’s outstanding eateries without too big a hit to your wallet. The idea for these is basically the same: Pre-fixe three-course dinners at bargain prices. Some of the restaurants may also include lunch, brunches and take-out.

Dine Out Lauderdale
When: Now through Sept. 30
Where: Various locations in Fort Lauderdale and Broward County
Web: visitlauderdale.com/dineout/
Miami Spice
When: Now through Sept. 30
Where: Participating restaurants in Miami Beach and Miami
Web: iLoveMiamiSpice.com

SEPTEMBER

OCCUPATION OF PALATKA — Long before the live oaks offered shade to visitors, the grounds of Palatka's Bronson-Mulholland House echoed with the footsteps of Union soldiers. Reconnect with the past at this annual Civil War living history event. Featuring educational exhibits, live weapons showcases and tours of the historic home, this gathering offers a rare glimpse into 1860s Florida for history buffs with the emphasis on Friday’s showing being geared specifically to students.
When: Sept. 25-27
Where: Palatka
Web: https://putnam-fl-historical-society.org/events/union-occupation-of-palatka

PENSACOLA SEAFOOD FEST — Bring a serious appetite and your best ’80s dance moves to this year’s annual fest. With over 150 artisan vendors, a powerhouse lineup of rising musical talent, and a culinary spread ranging from crawfish mac and cheese to conch fritters, Pensacola’s annual rite of fall promises non-stop flavor and entertainment headlined by Saturday night's main event, The Molly Ringwalds. The rest of the live music lineup, which always features up-and-coming artists (ie. future Grammy-award winners), has yet to be announced. Also includes the Gulf to Table local chef showcase of inspired seafood bites, three days of chef demos and landlubber fest classics like chicken tenders, bloomin’ onions, turkey legs and funnel cake.
When: Sept. 25-27
Where: Pensacola
Web: https://www.pensacolaseafoodfestival.com

FIVE FAB FESTS FOR FOODIES! – You can eat your way across South Florida (both coasts) at some of the region’s outstanding eateries without too big a hit to your wallet. The idea for all of these is basically the same: Pre-fixe three-course lunches and dinners at bargain prices. Some of these may also include brunches and take-out.

Sizzle Dining
When: Sept. 1-3
Where: Throughout Lee and Collier Counties
Web: sizzledining.org
Delray Beach Restaurant Month
When: Sept. 1-30
Where: Various locations in downtown Delray Beach
Web: downtowndelraybeach.com/restaurantmonth
Dine Out Lauderdale
When: Now through Sept. 30
Where: Various locations in Fort Lauderdale and Broward County
Web: visitlauderdale.com/dineout/
Flavor South Florida
When: Sept. 1-30
Where: Throughout Palm Beach County
Web: flavorpb.com
Miami Spice
When: Now through Sept. 30
Where: Participating restaurants in Miami Beach and Miami
Web: iLoveMiamiSpice.com

LABOR DAY IN THE PARK – There is no set theme for this annual gathering, but it is a whole lot of fun. The biggie event, of course, is the parade, but there are also musical performances, vendors, food trucks and lots of activities for the youngsters.
When: Sept. 7
Where: Settlers Park and Seminole Park, Okeechobee
Web: okeechobeemainstreet.org/labor-day-festival/

ENGLEWOOD PIONEER DAYS – If you haven’t yet visited this charming community in Southwest Florida, this would be a good time to go. It’s a celebration of the town’s history, especially the early settlers from the late 1800s. The biggie events are on Labor Day and include a parade, a diaper derby, pie-eating contest, a watermelon-eating contest, a long beard contest, lots of activities for the kids and live music. There also events in the week leading up to Labor Day, including a Little Miss and Mister pageant, a Miss Englewood pageant and cardboard boat races.
When: Sept. 5-7
Where: Various locations in Englewood
Web: englewoodchamber.com/pioneer

ISLAND HOPPER SONGWRITER FEST – From downtown hotspots in Fort Myers to tiki bars along the beaches and islands, you will enjoy venues as varied as the performers at this 10-day festival. Some 60 performers will participate. Most of the shows are free and at smaller venues. The headliners this year are Edwin McCain, LOCASH, Michael Ray and Alexandra Kay. Behind many great country music hits, there is often another outstanding singer/songwriter who wrote the tune. Get to know the back stories behind country’s biggest hits and see them performed by the writers. You’ll be surprised to learn how many country music hits they wrote and/or the famous artists with whom they have performed. You won’t go wanting for food and drink, too, as many of the venues offer a variety of yummy fare.
When & Where: Sept. 18-20 on Captiva Island; Sept. 21-22 in Cape Coral; Sept. 23-24 in downtown Fort Myers; Sept. 25-27 on Fort Myers Beach
Web: IslandHopperFest.com