Featured image alt text: Things to do in Southwest Florida October 2–4, 2026, including waterfront music, Oktoberfest, fall festivals and Gulf Coast activities.
October arrives with a full slate of things to do across Southwest Florida. This weekend brings international short films, beachfront music, Oktoberfest celebrations, live theater, comedy, family fall fun and even a coastal cleanup. Whether you are planning a date night, a day with the kids or a quick trip up the coast, here are some of the best events happening from Marco Island to Punta Gorda.
Marco Island
Manhattan Short Film Festival
When: Friday, October 2 at 5:30 p.m.; Saturday, October 3 from 2–4 p.m.
Where: Marco Island Center for the Arts, 1010 Winterberry Drive, Marco Island
Admission: $10–$15
Moviegoers become part of the jury at this global short-film showcase. Watch 10 finalist films from around the world, then cast your ballot for Best Film and Best Actor alongside audiences in hundreds of cities.
Friday Night Bingo
When: Friday, October 2 from 5–9 p.m.
Where: San Marco Catholic Church Parish Hall, Marco Island
Ease into the weekend with a classic community bingo night. It is an easygoing Friday outing for regular players and newcomers alike.
Sanibel and Captiva
Captiva Coastal Cleanup
When: Saturday, October 3 from 9:30 a.m.–12:30 p.m.
Where: McCarthy’s Marina, 11401 Andy Rosse Lane, Captiva
Admission: Free; advance registration recommended
Help care for Captiva’s coastline by collecting debris on foot, by kayak, paddleboard or boat. Lunch begins at noon, and the first 40 registered volunteers may be able to join the cleanup by Captiva Cruises boat.
Naples
One Night in Memphis
When: Saturday, October 3 at 7:30 p.m.
Where: Hayes Hall at Artis—Naples, 5833 Pelican Bay Boulevard, Naples
Admission: Ticketed
Travel back to the legendary 1956 Sun Studio jam session shared by Elvis Presley, Johnny Cash, Jerry Lee Lewis and Carl Perkins. This 90-minute concert blends rockabilly, gospel and country with a live band and favorite early rock ’n’ roll songs.
Sunset Silent Disco on the Beach
When: Friday, October 2 from 6–8 p.m.
Where: Lowdermilk Park, 257 Banyan Boulevard, Naples
Admission: Ticketed
Start with guided breathwork and crystal singing bowls, then put on wireless headphones and dance as the sun sets over the Gulf. It is part wellness session, part beach party.
Comedy at Off The Hook
When: Brad Upton on Friday, October 2; Vinny Guadagnino on Saturday, October 3
Where: Off The Hook Comedy Club, 2500 Vanderbilt Beach Road, Naples
Admission: Ticketed; showtimes and prices vary
Naples has two distinct comedy options this weekend: veteran stand-up Brad Upton on Friday and television personality Vinny Guadagnino on Saturday. Check the club calendar for individual showtimes and age requirements.
Bonita Springs and Estero
Dear Evan Hansen
When: Friday, October 2 at 7 p.m.; Sunday, October 4 at 2 p.m. and 7 p.m.; performances continue through October 11
Where: Arts Bonita Performing Arts Center, 10150 Bonita Beach Road, Bonita Springs
Admission: $15–$35; recommended for ages 13 and older
Arts Bonita opens its production of the Tony Award-winning musical about connection, belonging and the consequences of a lie that grows beyond one teenager’s control.
Los Tigres del Mundo at Hertz Arena
When: Saturday, October 3 at 8 p.m.; doors open at 6:30 p.m.
Where: Hertz Arena, 11000 Everblades Parkway, Estero
Admission: Tickets start at $53.84; parking is additional
Hertz Arena welcomes Los Tigres del Mundo for a Saturday-night concert in Estero. The arena is cashless, so plan accordingly for parking and on-site purchases.
Farmer Mike’s Fall Festival and Haunted Maze
When: Saturday, October 3 from 9 a.m.–10 p.m.; Sunday, October 4 from 9 a.m.–9 p.m.; the haunted maze begins Saturday night
Where: Farmer Mike’s U-Pick, 26031 Morton Avenue, Bonita Springs
Admission: Timed tickets sold online
Make a full day of the farm’s corn mazes, hayrides, bounce houses and seasonal U-pick fun, including pumpkins and sunflowers. After dark on Saturday, the maze takes a spooky turn.
Reserve a time at Farmer Mike’s
Steel’n Peaches: Allman Brothers Tribute
When: Saturday, October 3 from 7–10 p.m.
Where: Sugarshack Downtown, 27421 Old 41 Road, Bonita Springs
Admission: Check the venue listing
Settle in for an evening of Southern rock as Steel’n Peaches celebrates the music and improvisational spirit of the Allman Brothers Band.
Fort Myers Beach
ParrotPhest Trop Rock Weekend
When: Thursday, October 1 through Sunday, October 4
Where: Margaritaville Beach Resort, 251 Crescent Street, Fort Myers Beach
Admission: Many performances are free
ParrotPhest fills the resort with four days of breezy trop-rock music and beachfront fun. Weekend performers include Rudy Cox, Monallo Band, Otis and The Beachcombers, Orlando Phillips and more across several resort venues.
See the official ParrotPhest schedule
Fort Myers
10th Annual Millennial Oktoberfest
When: Friday, October 2 at 4 p.m. through Sunday, October 4 at 6 p.m.
Where: Millennial Brewing Company, 1811 Royal Palm Avenue, downtown Fort Myers
Admission: Check the event listing
Millennial Brewing marks a decade of Oktoberfest celebrations with German food, special beers, eating competitions, live entertainment, games and anniversary merchandise.
Stormy Daniels at Snappers Laugh In
When: Saturday, October 3 at 6 p.m.
Where: Snappers Laugh In Comedy Club, Fort Myers
Admission: Ticketed; adults only
Stormy Daniels brings an adults-only stand-up set to Snappers for one Saturday-night performance. Check the listing for ticket availability and entry policies.
Cape Coral
Mean Girls: The Musical
When: Opens Friday, October 2 and runs through October 17; matinees at 2 p.m. and evening performances at 7:30 p.m.
Where: The Belle Theatre, 2708 Santa Barbara Boulevard, Suite 135, Cape Coral
Admission: Reserved seating is $25
The hit movie comes to the stage in a sharp, energetic musical about navigating popularity, friendship and high school. The production includes mature language and themes.
Fueled by Fire 5K
When: Saturday, October 3; 7 a.m. start
Where: Tarpon Point Marina, 5902 Silver King Boulevard, Cape Coral
Admission: Registration required
Run or walk a scenic waterfront 5K while supporting the Cape Coral Fire Department Community Foundation and its fire-safety education and community programs.
Register through the foundation
Punta Gorda
German-American Oktoberfest at Fishermen’s Village
When: Saturday, October 3 from noon–8 p.m.
Where: Fishermen’s Village, 1200 West Retta Esplanade, Punta Gorda
Admission: Free admission and parking
Celebrate on the Charlotte Harbor waterfront with a 20-piece German band, traditional food, beer and activities for children. It is an easy all-ages way to enjoy Oktoberfest without leaving the coast.
See Fishermen’s Village events
Prana Farms Pumpkin Festival
When: Friday through Sunday from 11 a.m.–6:30 p.m.; open Thursday through Sunday throughout October
Where: Prana Farms, 6026 Sweden Boulevard, Punta Gorda
Admission: $10 per person; free parking
Pick out a pumpkin and stay for the petting zoo, butterfly exhibit, bounce houses, cider, ice cream and other family activities. It is a relaxed way to bring a little fall spirit to sunny Southwest Florida.
Make the Most of Your Southwest Florida Weekend
This weekend makes it easy to mix classic Gulf Coast experiences with the first signs of fall. Pair a morning cleanup or 5K with a waterfront lunch, take the family to a pumpkin festival, or turn Saturday night into a concert, musical or comedy outing.
Event details can change, and some activities require advance tickets or registration. Confirm times, prices, age restrictions and availability with the organizer before heading out.
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