As September rolls in, Southwest Florida welcomes a vibrant mix of food, festivals and fall traditions. Sizzle Dining returns with more than 90 restaurants offering curated menus for a good cause, while the Island Hopper Songwriter Fest fills coastal venues with stories and song. From the spirited blessing of Everglades City’s stone crab fleet to comedy shows, murder mysteries and Oktoberfest cheer, this September is packed with personality. Whether you’re wandering a wetland, navigating a corn maze or toasting with a local brew, there’s no shortage of ways to savor the month.
Sept. 3-30
Sizzle Dining, Various Locations in Southwest Florida
Sizzle Dining returns, showcasing special prix-fixe menus at more than 80 participating restaurants across Southwest Florida. The four-week dining event highlights the region’s culinary diversity, with options ranging from upscale dining to casual favorites. Each meal includes a multi-course experience at a fixed price point, and proceeds support Blessings in a Backpack, a nonprofit dedicated to feeding school-aged children in need. See More
Sept. 5
Voices of the Everglades: Entangled in the Mangroves at Artis—Naples
This special panel brings together artist Nathalie Alfonso, Miccosukee Tribe sustainability officer Kevin Cunniff, environmental scientist Kathy Worley of the Conservancy of Southwest Florida and Rookery Bay National Estuarine Research Preserve’s director, Jeffrey Carter. Guided by moderator Rev. Houston Cypress from the Otter Clan, the group shares diverse perspectives on how art and environmental stewardship intersect in the River of Grass, inspired by the immersive exhibition in Artis—Naples, The Baker Museum. See More
Sept. 13
The Magic of Motown at Barbara B. Mann Performing Arts Hall, Fort Myers
The golden era of soul comes to life with The Magic of Motown, a high-energy tribute to legendary acts like The Jackson 5, The Temptations, Aretha Franklin and Diana Ross. Complete with dazzling costumes and choreography, this show brings timeless classics to life for one night only. See More
Sept. 19 and 20
Comedian Desi Banks Live at Off the Hook Comedy Club, Naples
The social media star and stand-up comedian brings his viral brand of humor to Naples for a two-night performance. Known for his quick wit and crowd work, the Atlanta native is a rising name in comedy with millions of followers and an electric live stage presence. See More
Sept. 19–28
Island Hopper Songwriter Fest, Fort Myers Beach, Captiva & Downtown Fort Myers
More than 70 national songwriters command waterfront bars, resorts and historic venues across Captiva Island, Fort Myers Beach and Downtown Fort Myers in this 10-day festival. Intimate acoustic sets, storytelling sessions and songwriter rounds provide music-lovers with inside looks at the creative process. See More
Sept. 20
Blessing of the Stone Crab Fleet at Camellia Street Grill, Everglades City
The Southwest Florida tradition marks the start of stone crab season with a ceremonial blessing of the boats and crabbers, and a celebration of the local fishing community. Organized by local churches and supported by the fishing industry, the event underscores the importance of maritime tradition and sustainability in Southwest Florida’s small fishing towns. See More
Sept. 20
Katt Williams at Hertz Arena, Estero
Veteran comedian and actor Katt Williams returns with his no-holds-barred stand-up act, tackling pop culture, politics and personal anecdotes with sharp social commentary and unmatched charisma. See More
Sept. 20
Matt Schofield at Arts Bonita, Bonita Springs
British guitar virtuoso Matt Schofield blends blues, jazz and funk in a genre-defying performance. Hailed as one of the best modern blues guitarists, the musician’s live shows are lauded for their fiery improvisation and soulful grooves. See More
Sept. 20
Wet Walk at Six Mile Cypress Slough Preserve, Fort Myers
Naturalists and Florida Gulf Coast University instructors Win Everham and Chad Evers embark on a guided walk through the wetlands at Six Mile Cypress Slough Preserve. This immersive outdoor experience offers a firsthand look at Southwest Florida’s fragile ecosystem. See More
Sept. 25
Crab Fest at Peace River Seafood & Crab Shack, Charlotte Harbor
Southwest Florida’s blue crab bounty with fresh seafood, live music and family fun at this local-favorite festival. Hosted by the beloved Peace River Seafood, Crab Fest brings a laid-back, Old Florida vibe to Charlotte Harbor’s waterfront. See More
Sept. 26 — Nov. 9 (weekends only)
Farmer Mike’s Fall Festival & Corn Mazes, Bonita Springs & Fort Myers
This harvesttime event runs weekends, with hayrides and three corn mazes—including a children’s maze, a larger, family-friendly maze and a haunted maze exclusively at the Bonita Springs farm for the brave of heart. Pumpkin and sunflower patches are ripe for the picking, while bounce houses, pedal bikes and axe throwing get the blood pumping. Local food vendors roll up alongside the on-site N’Season Cafe, which sells farm-fresh lemonade, milkshakes and light bites. See More
Sept. 27
Fort Myers Oktoberfest at The Standard Restaurant Downtown
Say ‘Prost!’ to German-inspired fare, local craft beers and live music in Downtown Fort Myers. Hosted by The Standard Restaurant, the festive gathering brings a Southwest Florida twist to the Bavarian tradition as attendees bar-hop throughout the River District. See More
Sept. 27
Mike Archer Live at Fishermen’s Village, Sunset Beach Club, Punta Gorda
Country music artist Mike Archer brings his feel-good tunes to the Sunset Beach Club at Fishermen’s Village. Set along the waterfront, this laid-back evening of live music pairs perfectly with sunset views and cold drinks. See More
Sept. 27
Shy Wolf Charity Golf Scramble, Heritage Bay Golf & Country Club, Naples
Guests support animal rescue efforts while hitting the links at this charity golf scramble benefiting Shy Wolf Sanctuary. The event includes contests, raffle prizes, lunch and a post-game awards ceremony—all in the name of healing hearts and saving lives. See More