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.
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
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.
Fort Myers
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.
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.
