October 2026 Events in Southwest Florida
If you've been waiting for the weather to break, October is your cue. From the biggest Oktoberfest in the region to a waterfront seafood festival and a film festival that brings filmmakers from around the world, here are five events worth putting on your calendar.
Yappy Hour: Spooky Edition
Dress your pup in their best Halloween costume and head to Center Court at Bell Tower Shops for a Halloween-themed Yappy Hour. Dog lovers can mingle, sip, snack, and stroll the shops while supporting a good cause — the event benefits the Gulf Coast Humane Society.
Bell Tower Shops is located at 13499 S. Cleveland Ave., Fort Myers.
View Event Details →Scarecrows in the Park
A beloved fall tradition for local families, Scarecrows in the Park fills Lakes Park with handmade scarecrows built by community members, businesses, and youth groups. This year's theme is "Scarecrows at Work," and the display is part of the larger Lakes Park Fall Festival, which also includes train rides, hayrides, bounce houses, and food.
All proceeds go directly back to the park, so a weekend outing doubles as a way to support one of Lee County's favorite green spaces. Lakes Park is located at 7330 Gladiolus Drive, Fort Myers.
View Event Details →Cape Coral Oktoberfest
Right in our own backyard, the German American Social Club hosts what's billed as Southwest Florida's largest Oktoberfest across two full weekends. Expect authentic German food, imported beer, live bands, dancing, and Volksfest performances, plus a children's carnival, rides, games, and local craft vendors.
Hours run Fridays from 4 PM to midnight, Saturdays from noon to midnight, and Sundays from noon to 8 PM. The club is located at 2101 SW Pine Island Rd, Cape Coral.
View Event Details & Tickets →Naples International Film Festival
Each October, Artis—Naples becomes a gathering place for filmmakers, film lovers, and the stories that bring them together. It's a polished, cultured long weekend of screenings and conversation, and a perfect reminder of how much arts and entertainment Collier County has to offer.
View Event Details →Naples Stone Crab Festival
Now in its 17th year, the Stone Crab Festival is a Naples waterfront tradition. The party kicks off Friday at 5 PM with the ceremonial cracking of the first stone claw, followed by live music, and continues all weekend with fresh seafood, arts and crafts vendors, and entertainment.
It's also a great excuse to explore the shops, restaurants, and attractions along the historic Naples waterfront. This year's festival is a proud partner of Honor Flight Network.
View Event Details →Why This Matters If You're Buying or Selling in SWFL
Events like these are a snapshot of what makes Cape Coral, Fort Myers, Naples, and the communities around them such special places to put down roots. A calendar this full of community, culture, and good food is exactly what many buyers and relocating families are hoping to find. If you're thinking about making Southwest Florida home, we'd love to show you around — neighborhoods and all.
Event dates, times, and ticket details can change. Please confirm directly with each organizer before heading out.
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