October brings a full calendar of festivals, outdoor markets, waterfront celebrations and seasonal activities to Southwest Florida. From Marco Island’s month-long breast cancer awareness campaign and Fort Myers Beach’s trop-rock weekend to major Oktoberfest celebrations in Cape Coral, Fort Myers, Naples and Punta Gorda, there are plenty of reasons to get out and explore.
Here are some of the top things to do in Southwest Florida during October 2026, organized by community from Marco Island to Punta Gorda.
Marco Island
Sixth Annual Paint the Town Pink
When: Throughout October; participating businesses decorate October 1–24
Where: Participating businesses across Marco Island
Marco Island turns pink for Breast Cancer Awareness Month as local businesses and community members decorate storefronts, offices and public spaces. Hosted by the American Cancer Society and Marco Island Area Chamber of Commerce, the island-wide campaign supports breast cancer awareness and research.
View Paint the Town Pink details
Sanibel Island
Annual Pink Out Picnic: Health & Hope Expo
When: Thursday, October 22, from 11:30 a.m. to 1:30 p.m.
Where: 2173 Periwinkle Way, Sanibel
Gather with the Sanibel community for a picnic and health expo held in recognition of Breast Cancer Awareness Month. The event brings neighbors together around health, hope and community support.
Naples
RocktoberFest 2026
When: Saturday, October 10, from 6:00 to 9:00 p.m.
Where: The Cove Outdoor Bar at Paradise Coast Sports Complex, 3920 City Gate Blvd. N., Naples
Admission: General admission is free; $45 VIP experience available
Oktoberfest meets rock night as local favorite Rock Republic takes the stage for an energetic evening of live music, German-inspired food, seasonal drinks and community fun. The VIP option includes exclusive seating, a light buffet, two drink tickets and access to a private bar.
Bonita Springs & Estero
Hopetoberfest SWFL Pub Crawl
When: Thursday, October 1, from 5:00 to 9:00 p.m.
Where: Begins at Ceremony Brewing, 10441 Packinghouse Lane, Bonita Springs
Admission: Ticket required; availability is limited
Raise a glass for a good cause during this three-stop Bonita Springs pub crawl benefiting Hope for Haiti’s healthcare programs. Guests begin at Ceremony Brewing before visiting two surprise locations, with a featured drink, light bites and raffles along the way.
View Hopetoberfest details and tickets
Oktoberfest 2026: Prost with a Purpose
When: Saturday, October 10, from 3:00 to 7:00 p.m.
Where: Riptide Brewing Company, 28120 Hunters Ridge Blvd., Bonita Springs
Admission: $35 for adults; $15 for children ages 3–12; free for children under 3
The Rotary Club of Bonita/Naples hosts a family-friendly Oktoberfest featuring the 20-piece Hafenkapelle German band, traditional Bavarian food, craft beer and dancing. Proceeds support charitable organizations serving the Bonita Springs and Naples area.
View Prost with a Purpose details and tickets
Fort Myers Beach
ParrotPhest Trop Rock Weekend
When: Thursday, October 1, through Sunday, October 4
Where: Margaritaville Beach Resort, 251 Crescent St., Fort Myers Beach
Admission: Many performances are free
Enjoy four days of laid-back island music during ParrotPhest at Margaritaville Beach Resort. The weekend includes trop-rock performers, a Parrot Pageant costume contest and a charity raffle benefiting the Alzheimer’s Association. Many performances at the License to Chill and La De Dah venues are free.
Fort Myers
10th Annual Millennial Oktoberfest
When: Friday, October 2, through Sunday, October 4
Where: Millennial Brewing Company, 1811 Royal Palm Ave., downtown Fort Myers
Millennial Brewing celebrates a decade of Oktoberfest festivities with German-inspired food, craft beer, competitions, games, live entertainment and special anniversary merchandise. Check the organizer’s event listing for daily opening and closing times.
View Millennial Oktoberfest details
Belltober Pub Crawl
When: Friday, October 2, from 6:00 to 9:00 p.m.
Where: Bell Tower Shops, 13499 S. Cleveland Ave., Fort Myers
Admission: $30
Taste your way through six Bell Tower restaurants during one festive evening. The crawl offers an easy way to explore the center’s dining scene while enjoying Oktoberfest-inspired food and drinks.
View Belltober Pub Crawl details
Yappy Hour: Spooky Edition
When: Friday, October 9, from 6:00 to 8:00 p.m.
Where: Center Court at Bell Tower Shops, 13499 S. Cleveland Ave., Fort Myers
Bring your costumed pup to Bell Tower’s Halloween-themed Yappy Hour. Dog lovers can mingle, sip, snack and stroll the shops during this pet-friendly fundraising event benefiting Gulf Coast Humane Society.
Fall at the Farm: Market & Music
When: Saturday, October 10, from 10:00 a.m. to 3:00 p.m.
Where: Buckingham Farms, 12931 Orange River Blvd., Fort Myers
Admission: Free
Spend a fall day on the farm browsing local vendors, enjoying live music and taking in the relaxed rural atmosphere at Buckingham Farms.
Oktoberfest at Fort Myers Brewing Company
When: Thursday, October 15, through Sunday, October 18; daily hours vary
Where: Fort Myers Brewing Company, 12811 Commerce Lakes Drive, Suite 28, Fort Myers
Admission: Free; family- and dog-friendly
Fort Myers Brewing Company hosts four days of Oktoberfest fun with more than 50 beers and hard seltzers, live bands, food trucks, commemorative merchandise and a free stein-hoisting competition. Consult the brewery’s event page or social channels for the final daily schedule before attending.
View Fort Myers Brewing Company Oktoberfest information
Docktoberfest
When: Friday, October 16, from 5:00 to 7:00 p.m.
Where: MarineMax Fort Myers, 14030 McGregor Blvd., Fort Myers
Admission: Free
Celebrate fall by the water during this Bavarian-themed evening at MarineMax Fort Myers. The relaxed waterfront setting makes it an easy Friday-night stop.
Cape Coral
Cape Coral Oktoberfest
When: October 16–18 and October 23–25; Fridays from 4:00 p.m. to midnight, Saturdays from noon to midnight and Sundays from noon to 8:00 p.m.
Where: German American Social Club, 2101 SW Pine Island Road, Cape Coral
Southwest Florida’s largest Oktoberfest returns for two weekends of German food, imported beer, live bands and dancing. The festival includes three entertainment stages, two dance floors, a children’s carnival, rides, games, handmade crafts and local vendors. General-admission and VIP ticket options are available.
View Cape Coral Oktoberfest details and tickets
Cape Coral Cyclones Fall Festival
When: Saturday, October 24, from 9:30 a.m. to 4:30 p.m.
Where: Cape Coral Sports Complex, 1510 Sports Blvd., Cape Coral
Spend the day enjoying games, activities, local vendors and food at this family-oriented fall festival hosted at the Cape Coral Sports Complex.
View Cape Coral Cyclones Fall Festival details
South Cape Spooktacular Pub Crawl
When: Saturday, October 24, beginning at 7:00 p.m.
Where: Participating venues throughout the South Cape entertainment district
Admission: Approximately $23; age restrictions apply
Put on your Halloween costume and explore participating South Cape bars during this seasonal pub crawl. Confirm check-in information, participating locations and ticket inclusions before attending.
View South Cape Spooktacular Pub Crawl details
Punta Gorda
German American Oktoberfest at Fishermen’s Village
When: Saturday, October 3, from noon to 8:00 p.m.
Where: Fishermen’s Village, 1200 W. Retta Esplanade, Punta Gorda
Celebrate Oktoberfest along Charlotte Harbor at Fishermen’s Village. The waterfront setting, restaurants, shops and German-themed entertainment make this a festive early-October outing.
View Fishermen’s Village event information
4th Annual Pumpkin Festival at Prana Farms
When: Select dates October 1–29, opening at 11:00 a.m.; confirm the operating calendar before visiting
Where: Prana Farms, 6026 Sweden Blvd., Punta Gorda
Admission: $10 per person; free parking
Pick pumpkins and enjoy a petting zoo, pony rides, hayrides, bounce houses and a butterfly exhibit during this family-friendly farm festival. Because operating days and hours may vary, check the event listing before making the trip.
View Prana Farms Pumpkin Festival details
3rd Annual Neighborhood Fall Festival & Nonprofit Expo
When: Saturday, October 17, from noon to 4:00 p.m.
Where: Laishley Park, 100 Nesbit St., Punta Gorda
Admission: Free
The City of Punta Gorda and Punta Gorda Chamber of Commerce bring the community together for food, games, crafts, a dessert walk and live entertainment. Visitors can also meet representatives from local nonprofit organizations and learn how they serve the area.
View Neighborhood Fall Festival details
Kalin’s Fall Festival
When: Saturday, October 17, from noon to 7:00 p.m.
Where: Kalin’s Farmers Market, 6187 Alan Blvd., Punta Gorda
Enjoy hayrides, pumpkin painting, a petting zoo, pony rides, craft vendors and food during a full afternoon of family-friendly fall activities.
View Kalin’s Fall Festival details
Spooktacular Fall Market
When: Saturday, October 24, from 10:00 a.m. to 2:00 p.m.
Where: Laishley Park, 100 Nesbit St., Punta Gorda
Browse seasonal merchandise and local vendors at this outdoor fall market beside Charlotte Harbor. The waterfront location makes it a pleasant stop during a Saturday in downtown Punta Gorda.
View Spooktacular Fall Market details
Make the Most of October in Southwest Florida
Whether you want to raise a stein at Oktoberfest, hear live music by the Gulf, take the kids to a pumpkin festival, support a community cause or shop an outdoor market, October offers something for nearly every interest. Many of these events take place outdoors, so keep the weather in mind and verify the latest schedule before heading out.
Event dates, hours, prices and availability can change. Use the links above to confirm the latest information directly with each organizer, especially for ticketed events and multi-day festivals.
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