Fall sweeps over the Gulf Coast, bringing with it a slate of must-do events. In Cape Coral, the largest Oktoberfest in Southwest Florida draws thousands of visitors over two weekends. Over in Estero, The Doobie Brothers perform five decades’ worth of their rock hits. And in Naples, original monochrome Rembrandt prints grace the Naples Art Institute’s gallery walls. Don’t miss these October events.
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Sep. 15, 2026 - Oct. 25, 2026
Forever Everly: The Everly Brothers Rockumentary
A multimedia musical that leverages documentary footage as its backdrop, Forever Everly relives the story of the Everly Brothers, from the height of success to the bands they influenced.
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May 12, 2026 - Oct. 29, 2026
Through the Light of the Estuary
Rookery Bay National Estuarine Research Reserve
United Arts Collier and Friends of Rookery Bay host this mixed-media exhibit with works inspired by the way light moves through Southwest Florida’s coastal environs.
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Oct. 16, 2026
Farmer Mike’s Fall Festival & Corn Mazes
Farmer Mike’s all-ages seasonal attractions are an autumn staple in Lee County.
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Oct. 02, 2026 - Oct. 15, 2026
Dark Art
Sidney & Berne Davis Art Center
The mysterious, surreal and alternative realities come alive at this grim exhibition, blending visual, performing and interactive arts.
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Oct. 02, 2026 - Oct. 31, 2026
Passage: A Themed Members Show
In the Main Gallery, Alliance artists convey what the word passage means to them, be it the changing of the seasons, aging or abstract visualizations of emotions.
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Oct. 03, 2026 10:00 a.m.
Blessing of the Stone Crab Fleet at Camellia Street Grill
This annual ritual marks the beginning of stone crab season along the Barron River.
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Oct. 03, 2026 6:00 p.m.
Candlelight: Tribute to Fleetwood Mac
Fever’s Candlelight Concert this month delves into the discography of one of America’s most beloved rock bands, still widely recognized after nearly 60 years since its creation.
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Oct. 05, 2026 - Nov. 24, 2026
Life Beneath the Ruins
Marco Island Center for the Arts
Florida-based artists Jean Camposano, Nancy Norman, Joel Shapses and Dick James showcase black-and-white clay and stone works, complementing a gritty series from photographer James Pryor.
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Oct. 08, 2026 - Oct. 11, 2026
Cabaret
Florida Gulf Coast University Bower School of Music & the Arts
TheatreZone partners with FGCU’s TheatreLab to give students professional production experience.
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Oct. 08, 2026 - Oct. 25, 2026
The Pillowman
The Laboratory Theater of Florida
Winner of the Olivier Award—the highest honor in British theatre—this dark comedy is set in a totalitarian state, where a fiction writer is grappling with reality.
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Oct. 10, 2026 noon - 6:00 p.m.
International Culture Fest
Community members of all ages don culturally significant clothing and accessories to represent their nationalities at the Cultural Heritage Center of Southwest Florida.
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Oct. 10, 2026 - Jan. 24, 2027
Rembrandt: Masterpieces in Black and White - Prints from the Rembrandt House Museum
Rembrandt: Masterpieces in Black and White - Prints from the Rembrandt House Museum explores the extraordinary achievement of Rembrandt Harmenszoon van Rijn.
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Oct. 16, 2026 - Oct. 18, 2026
Cape Coral Oktoberfest
German-American Social Club of Cape Coral
Florida’s largest Oktoberfest takes over the Cape with authentic schnitzels, bratwursts and potato pancakes, plus stages for Volksfest performances.
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Oct. 17, 2026 - Feb. 14, 2027
The Surrealist International: Fifty Years of Dreams
Curated at the Tate in London and debuted in Paris, this exhibition makes it to only three American cities.
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Oct. 18, 2026
Healing Voices
Part of The Naples Players’ ArtRX, an initiative in partnership with NCH Naples Comprehensive Health that supports clinical care in the region through the arts, this show connects healthcare professionals and theatre performers.
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Oct. 21, 2026 8:00 p.m.
The Doobie Brothers ‘Walk this Road Tour’
An American rock band that began in 1970s California, The Doobie Brothers celebrate the 50th anniversary of their Takin’ It to the Streets album on this North American tour.
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Oct. 22, 2026 5:30 p.m.
Musical Interludes featuring Everton Vidal Azevedo
Marco Island Center for the Arts
Brazilian-born, Southwest Florida-based vocalist and guitarist Everton Vidal Azevedo blends bossa nova—a 1950s-era, lyrical Brazilian style—with pop lounge music at this intimate Marco Island concert.
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Oct. 22, 2026 - Oct. 25, 2026
Naples International Film Festival 2026
Each October, the Naples International Film Festival turns Artis—Naples into a gathering place for filmmakers, film lovers and the stories that bring them together.
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Oct. 23, 2026 - Nov. 22, 2026
The World Goes ‘Round
This revue celebrates composer John Kander and lyricist-playwright Fred Ebb.
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Oct. 31, 2026 10:00 a.m. - 4:00 p.m.
Día de los Muertos Celebration
This Mexican holiday honors deceased loved ones and shared memories through vibrant displays of art and music.
