Fall in Naples and Southwest Florida does not mean sweaters and falling leaves. It means pumpkin patches under palm trees, Halloween fun in the sunshine and live music on outdoor patios every night of the week. Here is your guide to what is happening from Friday, October 9 through Sunday, October 11.
Family Fun: Boo at the Zoo Opens at Naples Zoo
Boo at the Zoo returns to Naples Zoo at Caribbean Gardens on Saturday, October 10, and runs through October 26. This year the Zoo is bringing the movies to life, with costumed characters, trick-or-treating for kids 12 and under, a Pirate Expedition Cruise, princesses, superheroes, a dinosaur encounter, live shows and music. It is one of the most loved fall traditions in Naples.
Families looking for more seasonal fun can visit Farmer Mike's Fall Festival in Bonita Springs, the Lakes Regional Park Pumpkin Patch in Fort Myers, or Pioneer Pumpkin Palooza at the Immokalee Pioneer Museum on Saturday morning.
Live Music: Rocktoberfest and Sunday Night in Bonita Springs
Rock Republic, one of Southwest Florida's most popular local bands, headlines Rocktoberfest 2026 at The Cove Outdoor Bar at Paradise Coast Sports Complex on Saturday from 6 to 9 p.m. On Sunday evening, the Ben Allen Band plays Sugarshack Downtown in Bonita Springs from 6 to 9 p.m., an easy and memorable date night.
Country fans can catch Ty Myers on The Legal Tour at Hertz Arena Saturday at 7:30 p.m. The Music & Arts Community Center hosts candlelight tributes to The Beatles and Adele on Saturday evening. Live music also fills patios across the region all weekend, from Dogtooth Sports Bar and Blue Martini in Naples to The Promenade at Bonita Bay and Snook Inn on Marco Island.
Comedy, Theater and Culture
Steve Hytner, best known as Kenny Bania on Seinfeld, performs at Off the Hook Comedy Cafe Friday through Sunday. Carmen Ciricillo plays Snappers Comedy Cafe in Fort Myers Friday and Saturday. Inside Broadway comes to the Music & Arts Community Center Friday night, and Mud & Blues plays Arts Bonita. Master of American Glass is on view at East West Fine Art in Naples through October 16.
Food, Markets and the Everyday Good Life
Italian Fest takes over The Beer Bar at Seed to Table in Naples Saturday and Sunday. The Farmers Market at Miromar Outlets in Estero opens its new season Saturday, joining favorites like Third Street South, The Shoppes at Vanderbilt and the Promenade at Bonita Bay. On the active side, the City of Naples Halloween Hustle 5K runs Friday evening at Baker Park.
Looking ahead, the Naples International Film Festival comes to Artis Naples October 22 to 25, and the Stone Crab Festival returns to Historic Tin City October 23 to 25.
Why This Weekend Matters If You Are Considering Naples or Southwest Florida
October is when Southwest Florida starts gearing up for season. The calendar fills, restaurants get busier and the weather turns into the reason so many people fall in love with this place. A fall weekend here is spent outside, with family traditions, live music and good food all close to home.
If Naples has been on your mind, whether as a second home, a future move, or a place you are still getting to know, I am always happy to be a resource. Reach out anytime, or sign up for This Week in Paradise, my weekly guide to living, playing and owning in Southwest Florida, delivered to your inbox every Friday.
Diane Harris, Realtor and Luxury Properties Specialist
Serving Naples, Bonita Springs, Estero, Marco Island, Collier County, Lee County and the surrounding Southwest Florida area
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