Live Music in Southwest Florida: October 22-29, 2026

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A live band performing on a string-lit outdoor amphitheater stage in Southwest Florida at dusk, with palm trees silhouetted against a deep blue and amber sky
Live Music · October 22, 2026

Live Music in Southwest Florida This Week: October 22-29, 2026

Catalina Quintero
Catalina Quintero Bilingual REALTOR · The Miranda Group · SL3635889

Looking for live music this week in Southwest Florida? From CAKE at an outdoor amphitheater in Fort Myers to the Gulf Coast Symphony playing The Lord of the Rings, a candlelit Halloween concert, two shows at Arts Bonita in Bonita Springs, the Naples Philharmonic performing Superman live, and free waterfront music on Marco Island, there is a show for most tastes between October 22 and 29. I rounded up eight shows that I could verify from each venue's or event's official page, with the artist, venue, date, time, and a ticket link for every one.

Key Takeaways

  • CAKE plays Caloosa Sound Amphitheater in Fort Myers Saturday, October 24 at 8:30 PM, with doors at 7 PM.
  • The Gulf Coast Symphony performs The Lord of the Rings at the Music & Arts Community Center Saturday, October 24 at 6 PM and 8 PM, with the full orchestra playing the film's score.
  • Candlelight: A Haunted Evening of Halloween Classics plays the Music & Arts Community Center in Fort Myers Friday, October 23 at 6 PM and 8:30 PM.
  • Arts Bonita in Bonita Springs hosts two concerts this week: blues artist Jason Ricci and The Bad Kind Friday, October 23 at 7:30 PM, then Classic Skynyrd Live, a Lynyrd Skynyrd tribute, Saturday, October 24 at 7:30 PM.
  • The Naples Philharmonic plays John Williams' Superman score live to the 1978 film Sunday, October 25 at 7:30 PM at Hayes Hall at Artis-Naples, closing the Naples International Film Festival.
  • Nick Smith plays Fort Myers Brewing Company Thursday, October 22 from 6 to 9 PM, and CJ's on the Bay on Marco Island hosts free Live Music Thursday from 6 PM on October 29.

Thursday, October 22

Fort Myers: Nick Smith at Fort Myers Brewing Company

The easiest show to catch tonight is at Fort Myers Brewing Company on Commerce Lakes Drive, where acoustic artist Nick Smith plays the taproom Thursday, October 22 from 6 to 9 PM. The brewery hosts live music most weeks in its open-air beer garden, and it is free to enter, family and dog friendly, with food trucks on site. The weekly live music schedule is on the Fort Myers Brewing Company live music page.

A Florida craft brewery beer garden at dusk with string lights over wooden picnic tables, a small acoustic band on a low patio stage, and palm trees against a purple-blue sky

Friday, October 23

Bonita Springs: Jason Ricci and The Bad Kind

Blues harmonica and guitar player Jason Ricci brings his band The Bad Kind to Arts Bonita in the Hinman Auditorium on Bonita Beach Road Friday at 7:30 PM. Ricci is a technically gifted player with a career in the blues, and the 400-seat theater makes it an up-close evening. Tickets start at about $39 on the Arts Bonita event page. The venue sits in the heart of Bonita Springs, an area covered in our Bonita Springs area guide.

Fort Myers: Candlelight Halloween classics

The Candlelight: A Haunted Evening of Halloween Classics concert plays the Music & Arts Community Center, home of the Gulf Coast Symphony, on Shire Lane Friday at 6 PM and again at 8:30 PM. A live string ensemble performs spooky and classical favorites by candlelight, a fitting warm-up for Halloween weekend. Tickets and session times are on the official Fever event page.

Saturday, October 24

Fort Myers: CAKE at Caloosa Sound Amphitheater

CAKE headlines Caloosa Sound Amphitheater on Edwards Drive in the Fort Myers River District Saturday night, with doors at 7 PM and the show at 8:30 PM. The alt-rock band behind hits like "Short Skirt / Long Jacket" and "The Distance" has toured steadily for decades, and this outdoor riverside amphitheater is one of the area's best places to hear a touring band. The event is presented with AEG Presents, and tickets are on the Caloosa Sound Amphitheater ticket page. If you are getting to know the Fort Myers area, our Fort Myers area guide covers the neighborhoods around the River District.

Fort Myers: the Gulf Coast Symphony plays The Lord of the Rings

Saturday evening the Gulf Coast Symphony performs The Lord of the Rings at the Music & Arts Community Center, with two shows at 6 PM and 8 PM. The full orchestra plays the sweeping score from the films live, a concert that works for film fans and classical audiences alike. Tickets run about $76 to $86, and details are on the Gulf Coast Symphony page.

A full symphony orchestra performing in a modern concert hall with warm amber stage lighting and a glowing cinema screen behind the musicians, with deep blue theater seating and gold accents

Bonita Springs: Classic Skynyrd Live

Saturday night at 7:30 PM, Classic Skynyrd Live, a Lynyrd Skynyrd tribute performed by Southern Steel, closes out a busy week at Arts Bonita in the Hinman Auditorium. The band recreates the southern rock catalog of "Sweet Home Alabama," "Free Bird," and the rest, in the same intimate theater that hosted the blues the night before. Tickets are on the Arts Bonita event page.

Sunday, October 25

Naples: Superman in Concert at Artis-Naples

The Naples Philharmonic closes the 18th annual Naples International Film Festival with Superman in Concert Sunday at 7:30 PM in Hayes Hall at Artis-Naples. The 1978 film screens with John Williams' score performed live by the orchestra under Principal Pops Conductor Jack Everly, a rare pairing of film and live music. Tickets and details are on the Artis-Naples events page. The campus sits in the Pelican Bay area of North Naples, covered in our Naples area guide.

Thursday, October 29

Marco Island: free live music at CJ's on the Bay

On Thursday, October 29, CJ's on the Bay, the waterfront restaurant at the Esplanade Shoppes on Marco Island, hosts its free Live Music Thursday from 6 PM. It is a low-key way to hear local musicians with the bay in the background, and the island's Chamber of Commerce events page lists the details. It is a dependable weekly stop if you live on or near the island, and our Marco Island area guide covers the neighborhoods and communities around the Esplanade.

A few more worth knowing about this week

Country artist Kylie Morgan brings her Healed Cowgirl Tour to The Ranch Concert Hall & Saloon in Fort Myers Thursday, October 29, with doors at 7 PM and the show at 8 PM; general admission is about $20 in advance, with tickets on the Ranch event page. The same venue also has a show Friday, October 23: JamWayne with Spyda JC and Trailer Trash Chris, doors at 7 PM and music at 9 PM. And Thursday, October 29 at 7:30 PM, the Naples Philharmonic opens its Masterworks series with Beethoven and Brahms in Hayes Hall at Artis-Naples, with pianist Yeol Eum Son under music director Alexander Shelley, details on the Artis-Naples events page.

How I put this list together

I keep this roundup to live music I can confirm from the venue's or event's own pages, and I link to the official ticket or event page for every show. I include concerts, tribute shows, orchestra and film concerts, brewery stages, and free outdoor sets across Naples, Bonita Springs, Estero, Fort Myers, and Marco Island. Lineups and times can shift, so it always pays to check the official page before you head out.

A note on fair housing: every venue, neighborhood, and home in Southwest Florida is open to everyone, and I am glad to help you find the place that fits you, whatever your story. If you are exploring a move here, a concert is a nice way to spend an evening in an area you might call home.

A note from the author: I'm Catalina Quintero, a bilingual REALTOR with The Miranda Group at Premiere Plus Realty, Co., serving Naples, Bonita Springs, Estero, Fort Myers, and Marco Island. I put this live music roundup together each week from current, published listings so you can find a show nearby. If you are thinking about a move, email or text me any time.

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Contact Catalina Quintero at (239) 206-6909 or use the contact page to schedule a consultation.