Top Things to Do in Southwest Florida in the Fall: 50+ Festivals, Art Shows & Seasonal Fun
- JujuG gurgelj23@gmail.com
- Oct 3
- 6 min read
When you think of fall, Southwest Florida may not be the first place that comes to mind. But locals know: autumn here is one of the most vibrant times of the year.
Cooler evenings, golden sunsets, and a packed calendar of festivals, art shows, farmers markets, and family fun transform Cape Coral, Fort Myers, Naples, and surrounding towns into seasonal playgrounds.
From pumpkin patches and Oktoberfest celebrations to art fairs, seafood festivals, and Halloween trunk-or-treats, this guide highlights 50+ top things to do in Southwest Florida in the fall.
Whether you’re a visitor or a year-round resident, these are can’t-miss activities that only happen once a year.
Top Things to Do in Southwest Florida in the Fall
Local Fall Festivals & Special Events by City
Below, you’ll find city-by-city fall festivals, fairs, and marquee happenings. (After this section, we’ll cover all the other seasonal activities.)
Cape Coral
The German-American Social Club hosts this multi-weekend festival featuring German foods, imported beers, live music spanning polka to country, dance floors, vendor booths, carnival rides, and craft exhibits.
Location: 2101 SW Pine Island Rd, Cape Coral
Harvest / Fall Festival at Mike Greenwell’s
This area event typically includes pumpkins, hayrides, live entertainment, local artisans, and seasonal decor (haunted hikes, corn maze). (Note: check each year’s schedule with local news sources.)
South Cape Spooktacular Pub Crawl
Join the costume-based adult event for a night of pub crawling throughout numerous bars throughout Cape Coral, include photo booth contest, complimentary drink and more.
Fort Myers
Lakes Park Fall Festival & Halloween Express
Throughout October, Lakes Park (7330 Gladiolus Dr, Fort Myers) offers a pumpkin patch, hayrides, bounce houses, children’s garden displays, the Halloween Express train, “Scarecrows in the Park” contest, themed photo stations, and family fun.
The historic estates in Fort Myers host a fall festival with craft & vendor booths, music, themed decor, family entertainment, and the usual tour attractions. (Often mid-October.)
Dark Art at Sidney & Berne Davis Art Center
Each October, the Sidney & Berne Davis Art Center opens its doors to the mysterious and macabre world of art, with surreal and dark art inspired exhibits.
Alliance for the Arts Curtain Call Carnage Haunted walk
Curtain Call Carnage haunted walk happens in October at the Alliance for the Arts.
Bell Tower Shops “Trick or Treat Spooktacular”
Trick-or-treating at shops, games, and seasonal decorations during a daytime event.
Calusa Nature Center Haunted Walk
The Calusa Nature Center's Annual Haunted Walk is a fundraising event held every Friday, Saturday, and Sunday in October. The half-mile-long walk features volunteer actors and spooky surprises along the trails and in different rooms.
Ghosts & Ghouls Candy Crawl at Gulf Coast Town Center
Gulf Coast Town Center’s annual Ghosts & Ghouls Candy Crawl is back on Saturday, October 25 from 5–8 PM in Fort Myers. Families can enjoy trick-or-treating, live entertainment, a costume contest with prizes, and spooky photo ops—all for free! Costumes are encouraged for this family-friendly evening of Halloween fun.
Barktoberfest & Pet Costume Contest
Join Gulf Coast Town Center on October 4 from 6–8 PM for Barktober Fest & Pet Costume Contest, a free family- and pet-friendly event. Enjoy music, photo ops, balloon art, and a costume contest with prizes benefiting the Gulf Coast Humane Society. Bring your furry friends and Halloween spirit for a night of fun!
Naples & Collier County
Naples Stone Crab Festival (October)
Celebrate the start of stone crab season with beachfront food stalls, live music, artisan booths, and family activities.
Cambier Park Fine Art & Craft Show
Running October through April on Saturdays, this downtown Naples event features local and regional artists offering original works, jewelry, ceramics, photography, and more.
Seasonal patch in the Mercato shopping district, with photo props, pumpkins, and fall décor.
Empowerment Farm Fall Festival
A farm venue near Naples hosts hayrides, petting zoo, pumpkins, games, and local food & crafts.
“Night Lights” at Naples Botanical Garden
Beginning in Nov/Dec, the garden transforms into a luminous evening experience with tropical plants lit by creative light displays (a late-fall extension).
A Halloween street festival on 5th Avenue South with performers, trick-or-treating among shops, and seasonal decorations.
Boo at the Zoo returns to Naples Zoo October 10–12 and 17–19, from 9 AM to 1 PM, with trick-or-treating for kids 12 and under. This year’s event brings movies and mythical magic to life with dinosaurs, pirates, unicorns, princesses, superheroes, live shows, and more for the whole family to enjoy.
The Annual Fall Festival and Corn Mazes at Farmer Mike's U-Pick consists of weekend festival activities and multiple corn mazes at both the Bonita Springs and Fort Myers locations. The festival is open on Fridays from 6 p.m. to 9:30 p.m., Saturdays from 9 a.m. to 10 p.m., and Sundays from 9 a.m. to 6 p.m..
Seasonal Nature & Outdoor Fall Activities
Beyond festivals, Southwest Florida offers nature-focused experiences best enjoyed in fall:
Fall Bird Migration Walks & Birding Tours
Join guided walks at CREW, Corkscrew, or local preserves to see migratory species arriving.
Mangrove Tunnel Kayak & Paddleboard Tours
In fall, temperatures are milder, bugs fewer, and waters calmer — perfect for eco tours.
SUP & Paddleboard in Quiet Estuaries
Explore hidden waterways, creeks, and back bays when summer traffic slows.
Wetland / Boardwalk Hikes (Six Mile Cypress, Picayune Strand, local preserves)
Trails and boardwalks through hammocks and cypress strands are most comfortable in fall’s milder weather.
Manatee Watching & Refuge Visits
Cooler water draws aquatic life into viewing zones; fall is a good time for refuge visits.
Sunset & Dolphin Cruises
Evening boat tours benefit from clearer skies, gentler breezes, and captivating light.
Shelling at Low Tide on Barrier Islands
Sanibel, Captiva, Marco: walk the tide line during early mornings when shells are fresh and fewer crowds.
Wildflower & Native Plant Bloom Surveys
Some native species bloom in autumn; preserves often host guided plant walks.
Stargazing Events
Lower humidity in fall enhances clarity for night sky events in conservation areas.
Picnics, Family Walks, Photography in Local Parks
Use local green spaces and waterfront parks when crowds are down and light is soft.
Halloween, Spooky, & Family Fun
Fall is prime time for spooky, whimsical, and costume-related fun. Here are seasonal options for families and thrill seekers:
Haunted corn mazes (Farmers Mike’s, farm venues).
Trunk-or-Treat Nights (Cape Coral City Hall, Naples Italian American Foundation, churches).
Costume contests at community centers, bars, or festival stages.
Pumpkin carving and decorating nights at libraries and schools.
Haunted hayrides in Cape Coral / Fort Myers parks.
Ghost tours in historic Fort Myers and Naples districts.
Halloween block parties (Naples 5th Avenue, neighborhood gatherings).
Scary storytelling evenings (arts centers, libraries and local book stores).
Rocky Horror Picture Show screenings in local indie theaters.
Spooktacular markets and Halloween-themed pop-up vendor nights (often at breweries or art spaces).
Food, Drink & Seasonal Flavor Experiences
Autumn brings special flavors, harvest influences, and festive menus in SWFL:
Stone Crab Season Kickoff (October) — waterfront restaurants feature fresh crab specials.
Sizzle Dining (September) — prix-fixe culinary events across multiple high-end restaurants.
Oktoberfest menus at craft breweries (e.g. Millennial Brewing in Fort Myers) and restaurants such as The Melting Pot .
Farm-to-Table / Harvest Dinners featuring local seasonal produce.
Seasonal pumpkin, apple, squash desserts at bakeries & cafes.
Oyster & shellfish festivals in coastal towns.
Wine tasting evenings, vineyard events.
Autumn beer and brew fests such as Cape Coral Oktoberfest.
Fall-themed food truck rallies and street food popups.
Coffee shops releasing pumpkin spice / fall specialty drinks.
Arts, Culture & Community Events
These activities highlight the creative and communal side of fall in SWFL:
Fort Myers Art Walks / gallery nights (first Fridays).
Naples Art After Dark (Crayton Cove galleries open evenings).
Outdoor movie nights with fall / Halloween lineups.
Artisan bazaars / holiday markets (starting in Nov/Dec).
Fall-themed paint & sip events.
Concerts & live music in parks or river districts.
Pop culture / comic cons (SW-FloridaCon etc.).
Night Markets (Alliance for the Arts in Fort Myers, seasonal evening markets).
Fall-Themed Photo Ops
Capture special seasonal shots at these places & moments:
Pumpkin patches & hay bale displays (Lakes Regional Park, Mercato, church patches).
Festival decorative stages and vendor booths.
Naples Pier at sunset with fall skies.
Sanibel Lighthouse dunes & beach grasses.
Six Mile Cypress boardwalks, reflections in water.
Fort Myers neon signs, murals and historic district facades.
Trails in preserves with filtered autumn light.
Night Lights at Naples Botanical Garden.
Waterfront docks, bridges, and mangrove tunnels (for silhouette shots).
Sample Day-by-Day Itinerary
Here’s how you could structure 3–4 days of fall in Southwest Florida:
Day 1 (Weekend): Cape Coral & Fort Myers
Morning: Pumpkin patch & hayrides at Lakes Regional Park
Lunch: Oktoberfest food trucks / German fare (if dates align)
Afternoon: Walk through vendor booths, live music, crafts
Evening: Fort Myers Art Walk / Night Market
Day 2: Nature & Coastal Escape
Early morning shelling on Sanibel
Midday: Mangrove kayaking or paddleboarding
Late afternoon: Birding tour in CREW / Corkscrew
Sunset: Dolphin cruise or pier walk
Day 3: Naples & Collier County
Morning: Naples Cambier Park Art Show
Lunch: Stone crab / seafood festival (October)
Afternoon: Mercato pumpkin patch + photo stops
Evening: Naples 5th Avenue Spooktacular or Night Lights
Day 4 (Optional): Spooky / Halloween Theme
Trunk-or-Treat event in the neighborhood
Haunted hayride / ghost tour in Fort Myers
Evening: Seasonal movie screening or costume contest
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