Southwest Florida is heading into a busy stretch of fall events, with everything from live music and family activities to theater, Halloween fun, and outdoor community events.

If you’re looking for something new to do over the next couple of weeks, here are five events happening across Naples, Bonita Springs, Estero, and Marco Island that are worth adding to your calendar.

Reel Nature: Kids Filmmaking Day

October 24 | Noon–4 PM
Lowdermilk Park, Naples

Young filmmakers can spend the afternoon learning how to tell stories through nature and video during this free outdoor workshop designed for children ages 7–14.

It’s a creative option for families looking for something a little different from the typical weekend activity and a great way for kids to explore both nature and storytelling.

Why we like it: It combines creativity, outdoor time, and one of Naples’ most recognizable Gulf-front settings.

Jason Ricci & The Bad Kind

October 23 | 7:30 PM
Arts Bonita Performing Arts Center, Bonita Springs

Blues fans have a great reason to head to Bonita Springs this week. Jason Ricci & The Bad Kind bring an energetic evening of blues and harmonica-driven music to Arts Bonita.

Ricci is known for his dynamic playing style, making this a strong pick for anyone looking for live music beyond the usual restaurant and bar scene.

Why we like it: It adds another layer to Bonita Springs’ growing arts and entertainment scene.

Mall-O-Ween

October 30 | 5–7 PM
Miromar Outlets, Estero

Miromar Outlets is getting into the Halloween spirit with Mall-O-Ween, a family-friendly evening featuring trick-or-treating, music, and costume contests for both children and pets.

It’s an easy option for families looking for a festive Halloween activity that combines entertainment with a little shopping and dining.

Why we like it: It’s casual, family-friendly, and convenient for families throughout the Estero and Bonita Springs area.

Packing Up Polly

Opens November 5
Arts Center Theatre, Marco Island

If you’re looking for a night of theater, Packing Up Polly opens November 5 on Marco Island and runs through November 22.

The comedy explores family, friendship, and reconnecting, offering a lighter entertainment option as the fall cultural season gets underway.

Why we like it: Marco Island continues to offer more than boating and beaches, and local theater is a great way to experience another side of the community.

Native Plant Giveaway & Sale

November 7 | 10 AM–1 PM
Estero RiverPark, Estero

Florida gardening gets a local focus at this Native Plant Giveaway & Sale. Visitors can shop native plants and wildflowers, learn more about Florida-friendly landscaping, and receive a free native plant while supplies last.

Preregistration is required for the free plant giveaway.

Why we like it: Native landscaping is especially relevant in Southwest Florida, where the right plants can support local wildlife and better handle our climate.

More Events to Watch

There are several other events worth keeping on your radar, including local theater in Naples, community walks, Halloween car shows, seasonal festivals, and more fall programming across Southwest Florida.

As the season gets busier, there will be even more happening throughout Naples, Bonita Springs, Estero, and Marco Island.

Planning Your Weekend?

Whether you’re looking for live music, family activities, theater, outdoor events, or something completely different, Southwest Florida offers plenty of reasons to get out and explore.

Which of these events is going on your calendar?

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