Looking for something fun to do in Southwest Florida this weekend? The final weekend of September brings live music to Fort Myers Beach, fall festivities to Bonita Springs, comedy in Marco Island and Punta Gorda, family fun in Cape Coral and one of Naples’ favorite farmers markets.
Here are some of the best events happening across Southwest Florida from Friday, September 25, through Sunday, September 27, 2026.
Marco Island
Tom Briscoe: It’s Not Mansplaining, It’s Old Mansplaining
When: Sunday, September 27, at 3:00 p.m.
Where: Arts Center Theatre, 1089 N. Collier Blvd., Suite 432, Marco Island
Admission: $35 for members and $40 for non-members
Spend Sunday afternoon laughing along with comedian Tom Briscoe as he shares his humorous “slants and rants” about being misunderstood by younger generations. The show covers marriage, travel mishaps, raising daughters, empty nesting, doctors, aging and plenty of unsolicited advice.
View show information and purchase tickets
Sanibel Island
BIG ARTS Ceramics Open Studio
When: Friday, September 25, from 9:30 a.m. to 12:30 p.m.
Where: BIG ARTS, 900 Dunlop Road, Sanibel
Admission: $25; available to currently registered students only
Currently registered BIG ARTS students can use the ceramics studio to continue and complete their artwork outside regular class hours. The monitored session offers extra creative time alongside other local artists. Space is limited, and advance registration is recommended.
View BIG ARTS Ceramics Open Studio details
Naples
Third Street South Farmers Market
When: Saturday, September 26, from 7:30 to 11:30 a.m.
Where: The parking lot behind Tommy Bahama on Third Street South, Old Naples
Admission: Free
Start Saturday morning at a Naples tradition that has connected local growers and independent merchants with the community since 1994. Shop for fresh produce, flowers, live plants, seafood, pasta, baked goods, prepared foods, jams, coffee and more—all from local and independent vendors, with no national chains.
View Third Street South Farmers Market details
Bonita Springs & Estero
Farmer Mike’s 12th Annual Fall Festival & Corn Mazes
When: Opening weekend is Saturday and Sunday, September 26–27; reserve a timed entry online
Where: Farmer Mike’s U-Pick, 26031 Morton Ave., Bonita Springs
Welcome fall in Southwest Florida with a five-acre corn maze, hayrides, bounce houses and seasonal photo opportunities. Guests can also enjoy pick-your-own sunflowers and pumpkins when available. Tickets are sold online in timed arrival windows, so purchasing in advance is recommended.
View Fall Festival details and reserve tickets
Fort Myers Beach
Island Hopper Songwriter Fest: Final Weekend
When: Friday, September 25, through Sunday, September 27
Where: Participating venues throughout Fort Myers Beach
Admission: Most performances are free; select events require tickets
The Island Hopper Songwriter Fest wraps up on Fort Myers Beach with performances by talented Nashville songwriters at resorts, parks, restaurants and waterfront venues. With dozens of shows scheduled throughout the weekend, visitors can build their own music-filled beach itinerary.
Weekend highlights include:
- Opening Showcase: Friday at 4:00 p.m. at Margaritaville Beach Resort, 251 Crescent St.; free.
- Bayside Park: Friday at 7:15 and 8:45 p.m.; Saturday at 2:45, 4:15 and 6:45 p.m.; free. Bring a chair.
- Music on the Mound: Saturday at 2:00 p.m. at Mound House, 451 Connecticut St.; ticket required.
- Pink Shell Pool Party featuring Michael Ray: Sunday at 5:30 p.m. at Pink Shell Beach Resort, 275 Estero Blvd.; ticket required.
View the complete Island Hopper schedule | Purchase Pink Shell Pool Party tickets
Fort Myers
Candlelight: ’90s Hip-Hop on Strings
When: Friday, September 25, at 8:30 p.m.
Where: Music & Arts Community Center – Gulf Coast Symphony, 13411 Shire Lane, Fort Myers
Age requirement: Ages 8 and older; guests younger than 16 must be accompanied by an adult
Experience ’90s hip-hop in an entirely different way as a string quartet performs music associated with artists such as Lauryn Hill, Outkast, The Notorious B.I.G. and 2Pac in an intimate candlelit setting. The approximately 60-minute concert combines familiar songs with the atmosphere of a classical performance.
View Candlelight concert details and tickets
Fort Myers Oktoberfest Bar Crawl
When: Saturday, September 26, from 4:00 to 10:00 p.m.
Where: Check-in at The Firestone Skybar & Martini Bar, 2224 Bay St., Fort Myers
Age requirement: 21 and older
Celebrate Oktoberfest in the Fort Myers River District with an evening bar crawl featuring participating downtown venues and drink specials. Check in at The Firestone before heading out to explore the night’s stops.
View Oktoberfest Bar Crawl details and tickets
Cape Coral
Touch a Truck
When: Saturday, September 26, from 10:00 a.m. to 1:00 p.m.; the first hour is a quieter sensory-friendly hour
Where: Cape Coral Chrysler Dodge Jeep Ram, 2200 NE Pine Island Road, Cape Coral
Admission: Free
Kids can get an up-close look at fire trucks, police vehicles and other impressive equipment during this free family event. Face painting, a bounce house and food trucks add even more fun, while the quieter opening hour offers a more comfortable experience for children with sensory sensitivities.
Bike Night + Full Moon Party
When: Saturday, September 26, from 5:00 to 9:00 p.m.
Where: Slipaway Food Truck Park & Marina, 1811 Cape Coral Parkway E., Cape Coral
Admission: Free
Enjoy a waterfront evening with motorcycles, live music from Model Citisin, approximately 10 food trucks and a full bar. A 50/50 raffle benefits a local nonprofit, and the event is family- and dog-friendly.
View Bike Night + Full Moon Party details
Punta Gorda
Food Truck Friday
When: Friday, September 25, from 4:00 to 7:00 p.m.
Where: Charlotte Harbor Trust Wealth Management, 310 Dupont St., Punta Gorda
Admission: Free; food available for purchase
Ease into the weekend with a casual community gathering featuring The Dawg Pound food truck and tables for relaxing with friends. Guests may bring their own drinks.
View Food Truck Friday details
The Library Comedy Club Show
When: Friday, September 25, and Saturday, September 26, at 7:30 p.m.
Where: Four Points by Sheraton Punta Gorda Harborside, 33 Tamiami Trail, Punta Gorda
Admission: Approximately $19; adults
Touring comedian Erik Lewin headlines two nights of stand-up comedy with Tim the Dairy Farmer and Joe Mahoney. It is an easy option for an adults-only night out along the Punta Gorda waterfront.
View The Library Comedy Club Show details and tickets
Make the Most of Your Southwest Florida Weekend
Whether you want to hear live music by the Gulf, get an early taste of fall, shop from local growers, entertain the kids or enjoy a night of comedy, Southwest Florida offers plenty of ways to fill the final weekend of September.
Event details can change because of weather, availability or organizer updates. Before heading out, use the links above to confirm the latest schedules, admission information and ticket availability.
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