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34 October Events for your Southwest Florida Calendar

Film festivals, Halloween activities and international musicians hit town this month.

BY September 26, 2023
Naples International Film Festival
2022 Naples International Film Festival, hosted at Artis—Naples. (Photo by Reagan Rule)

As the Gulf Coast swings into another stellar season, the monthly events ramp up. In Naples, Tin City kicks off the start of stone crab season with its annual festival. In Fort Myers, the regional premiere of thriller play Misery at The Laboratory Theater of Florida sends a chill down audiences’ spines. And, in Cape Coral, the city celebrates 10 years of its Spooktacular Trolley event, bringing guests the best drinks from local joints—all in good spirits. 


Now through Oct. 15

Naples Invitational at Naples Art Institute

Showcasing the talent of nearly 40 contemporary Naples artists, the biennial survey reflects the complexities and opportunities of today’s American experience. The show is dedicated to ceramic artist Gail Geary, who passed away during the opening weekend of the exhibition. Her three included pieces demonstrate the unique graphic expression that made her work part of important collections across the United States.

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Now through Oct. 28 

Hairspray at Broadway Palm, Fort Myers

With fresh relevance, Broadway’s Tony Award-winning musical comedy phenomenon follows the story of Tracy Turnblad, an aspiring dancer in Baltimore, as she fights for a chance for herself and others to follow their dreams at the peak of the civil rights movement.  

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Now through Nov. 15 

Pop of Pink at High Tide Studio & Gallery, Naples 

Inspired by the 2023 Pantone Color of the Year, the Barbie movie and Florida scenery, each work in the showcase features splashes of the titular color. Discover pieces such as Elaine Clarfield Gitalis’ abstracts with pink and purple hues or John Clarke’s realist interpretations of local landscapes as well as other works by local plein-air artists. The gallery partners with Path2Freedom for the show, gathering art supplies and donations for girls staying at Naples’ Magnolia House who have been rescued from sex trafficking.  

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Now through Dec. 2

Preserving Collier: 20 Years of Conservation Collier at Collier Museum at Government Center, Naples

In 2003, Collier County residents passed a measure to allocate tax funds for purchasing sensitive and threatened conservation lands throughout the county. As Conservation Collier celebrates 25 years, the county looks back on the acquisition and preservation of 4,000 acres in 22 preserves and lands. The exhibit explores the habitat and wildlife the program has worked to preserve.

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Now through Jan. 20

Ebbets in the Everglades: The Unusual Story of the World-Famous Photographer You Never Heard Of, Museum of the Everglades, Everglades City

If you do recognize the name Charles C. Ebbetts, it could be for his most famous photograph of workers lunching on a suspended I-beam above Manhattan—although he rarely gets credit for it, it’s declared one of Time Magazine’s 100 Greatest Images. As a pioneering photographer, Charles settled in South Florida in 1935, chronicling the wilderness of the Everglades and Keys for the Associated Press and National Park Service. This is the first museum exhibit dedicated solely to his body of work. 

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Oct. 4 – Nov. 11 

Steel Compositions – The Art of Metal at Aldo Castillo Gallery, Estero

Born in Argentina and based in Miami since 1995, abstract sculptor Carolina Sardi mounts a solo show of her labor-intensive wall sculptures crafted from raw steel. Sometimes playful, they reflect a deep connection with the universe spectators can interpret through the lens of their individual experiences.

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Oct. 4–22 

The Dining Room at Sugden Community Theatre, Naples

The heart of the home becomes the stage for a pageant of 60 characters from different families and time periods, all interwoven into an analogy of the vanishing upper middle class. Actor Jody Cameron plays 10 different characters, each with a different trauma or trigger associated with the dining room central to the family unit. “I have to pull from 10 different areas of my life to bring their stories to life,” he says. “The audience will be able to find a bit of themselves and their family in every story told.”

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Oct. 6  

Martina Long – Women of the 60’s at The Norris Center, Naples

United Arts Collier hosts this concert as Sarasota resident and professional vocalist Martina Long takes audiences on a sentimental, tuneful journey via the music of legends like Janis Joplin, Carole King and Tina Turner. She has traveled the world as a solo performer and part of the girl group Soul Sisters for various cruise lines.

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Oct. 6–8

Sailing Summerset Regatta, Fort Myers Beach

Created in 1965 by the Caloosahatchee Marching and Chowder Society, the annual yachtees’ tradition centers around the marinas of Fort Myers Beach, and this year joins the city’s post-hurricane recovery efforts. See buoy races on Saturday and distance races on Sunday.

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Oct. 7

Forest Bathing at Rookery Bay Research Reserve, Naples

Inspired by the Japanese shinrin-yoku practice, the guided, meditative experience takes place once a month along a scrub and mangrove trail at the Rookery Bay Environmental Learning Center. A Certified Forest Bathing Guide will conduct a guided meditation session that engages curiosity and the senses to connect with nature. The session includes light refreshments as part of a closing ceremony.

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Oct. 7 & 28 

Ancestor’s Table Exhibit at Immokalee Pioneer Museum at Roberts Ranch, Immokalee

The inclusive experience explores the Hispanic immigrant diaspora by reconnecting with ancestors and heritage through recipes and foodways. The cultural series begins with an opening reception and includes exhibit tours with demonstrations of native foods, such as chaya and tamales. 


Oct. 9 — Nov. 21

Natural Elements at Marco Island Center for the Arts, Marco 

This invitational exhibition incorporates clay, woven reeds, dry leaves, fossilized wood and other found environmental materials into wall mounts, pedestal pieces and jewelry. A highlight, artist Ran Adler’s loosely woven and embroidered linen occupies an entire gallery, immersing guests in the Earth’s beauty from indoors.

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Oct. 12

Foghat at Caloosa Sound Amphitheatre, Fort Myers

Picture it: Listening to “Fool for the City” outdoors overlooking the Caloosahatchee River with city lights twinkling in the background. For Caloosa Sound’s 2023-24 season opener, rock ‘n’ roll band Foghat takes the stage more than 50 years after their debut album to perform their biggest hits. 

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Oct. 12 — Nov. 5

26 Miles at Gulfshore Playhouse, Naples 

A late-night call from her estranged daughter, Olivia, begins Beatriz’s cross-country roadtrip and journey to reconnection and healing. As the pair travels from Philadelphia to Wyoming, the tension reaches a breaking point, leaving the audience wondering if they can fix what is broken. 

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Oct. 12–15

Heathers: The Musical at Florida Gulf Coast University Theatre Lab, Fort Myers

From the creative talent behind such classic comedies as Reefer Madness, Desperate Housewives and Legally Blonde comes the ultimate mean-girl musical, adapted from the cult ’80s flick. TheatreZone and Florida Gulf Coast University (FGCU)’s Bower School of Music & the Arts join forces to portray high school anxiety, humor and homicidal fantasy in Ohio.

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Oct. 13 — Nov. 16 

Citrus Flux at the FGCU’s Wasmer Gallery, Fort Myers

Three FGCU alumnae (Lauren Ashley S. Baker, Jessica Dehen, Karri Leamon) return to showcase a variety of artforms, including sculptures, paintings and videos. Having earned their masters of fine arts, the three artists currently teach and create at their respective learning institutions—lending their work the multi-dimensional perspective of artists, students and teachers. 

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Oct. 14 

Candlelight: Vivaldi’s Four Seasons & More at Music & Arts Community Center, Fort Myers 

Gulf Coast Symphony acts as the hub for the worldwide concert phenomenon; Vivaldi’s opus leads the lineup of masterpiece classics performed by the Listeso Strings, with thousands of candles illuminating the musicians as they play. 

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Oct. 14 — Jan. 7.

Frank Stewart’s Nexus: An American Photographer’s Journey at Artis—Naples, The Baker Museum

The photographer spent his career documenting Black culture in Africa, Cuba and America. As a senior staff photographer for the Jazz at Lincoln Center Orchestra, he captured live performances and personal moments of such greats as Miles Davis, Dizzy Gillespie and Wynton Marsalis. This first major museum exhibition of Stewart’s work exhibits on the Baker’s third floor. 

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Oct. 19–29

Radio Golf at Alliance for the Arts, Fort Myers

History butts head with progress in this culmination of August Wilson’s ten-play series chronicling the lives of Black Americans in the 20th century. The decade: 1990. The setting: Pittsburgh, where an ambitious real estate developer aspires to become the city’s first Black mayor. Radio Golf faces the dilemma of how change can threaten a community’s heritage. 

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Oct. 20-21

Comedian Kountry Wayne Live at Off the Hook Comedy Club, Naples

With millions of followers on social media, a Netflix comedy special and stages across the country, Kountry Wayne gathers a fan base with his patent brand of Southern-inspired humor, turning misfortune into laughter. 

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Oct. 20-22 & 27-29

Oktoberfest at German American Social Club, Cape Coral

The region’s biggest and most authentically German October festivities has it all: lederhosen, oompah bands, schnitzel and kraut, beer (lots of beer), and, of course, the chicken dance. Celebrating its 38th year of keeping German culture alive, it features nonstop live music on three stages.

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Oct. 20–29

The Rocky Horror Show at Fort Myers Theatre

The British musical show made famous by its film adaptation in 1975 predates it by two years. A parody of horror movies, it hits the Fort Myers stage for the second year with all the same shenanigans and characters – Brad, Janet and Dr. Frank-N-Furter. Every Friday and Saturday night of its run, the midnight show encourages the sort of cult audience participation (but no water guns) you’ve come to expect.  

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Oct. 20 — Nov. 12

Misery at The Laboratory Theater of Florida, Fort Myers

A perfect psychological thriller for Halloween season: Stephen King’s eponymous fright novel inspires the Arthur Goldman play with its ghoulish plot twists and turns. It adapts the 1990 horror film starring Kathy Bates, James Caan and Lauren Bacall, and the performance at The Lab marks the regional premiere of the show in Southwest Florida. 

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Oct. 21

Southwest Florida Symphony: Brave New Pops 1 – R.E.M. Explored at Barbara B. Mann Performing Arts Hall, Fort Myers

The concert brings together the immense talent of Emmy award-winning violinist Robert McDuffie and founding member of the classic rock band, bassist Mike Mills. It opens with the full symphony performing R.E.M. stapes and ends as the two headlining musicians perform “Concerto for Violin, Rock Band and Orchestra,” which Mills composed for McDuffie.

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Oct. 21 

South Cape Spooktacular, Cape Coral  

About a dozen eating and drinking establishments throughout the Downtown Cape Coral area participate in this 10th-annual event by serving drink samples and a candy treat to all the ghouls and bodies aboard the Drink-or-Treat Trolley. Sing, dance and win prizes along the spirited route. Upon request, designated drivers receive a complimentary nonalcoholic beverage at each location.

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Oct. 21–22

Art in the Wild at J.N. “Ding” Darling National Wildlife Refuge, Sanibel Island

Nine accomplished creators demonstrating, eight others leading workshops and hands-on art, five duck stamp celebrities presenting, and an estimated 20-plus plein-air artists competing: The inaugural nature-art event centers around the refuge’s art legacy. “Ding” Darling, a Pulitzer-winning editorial cartoonist, helped create the refuge and the Federal Duck Stamp Program. Wildlife artist and six-time Federal Duck Stamp winner Joe Hautman headlines alongside his two brothers, who are also multi-time winners.

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Oct. 22

Considering Matthew Shepard at Naples United Church of Christ

Choral Artistry performs Grammy Award-winner Craig Hella Johnson’s piece honoring the memory of Matthew Shepard, who passed away 25 years ago this month, as a victim of an anti-gay hate crime. Loosely modeled after Bach’s passion pieces, the three-part oratorio draws from journal writing, news clippings and interviews to create the libretto of Matthew’s life and legacy.

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Oct. 25 — Nov. 20 

Rush of Color at First Presbyterian Church, Bonita Springs

While Fort Myers Beach Art Association rebuilds its island home destroyed by Hurricane Ian, it hosts events throughout Southwest Florida, including this season-opening juried show representing a variety of mediums from watercolor to collage. The association foresees traveling its member exhibitions into 2025. 

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Oct. 24 — Nov. 12

The Legend of Georgia McBride at Arcade Theater, Fort Myers

Florida Repertory Theatre presents this belly-laugh musical about an Elvis impersonator who turns his act into a drag show. As “the King” turns into a queen, the music goes beyond Elvis to reprise hits by Loretta Lynn, Barbara Streisand, Katy Perry and a variety of other female voices.  

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Oct. 26–29

Naples International Film Festival at Artis—Naples

NIFF has celebrated novice and noteworthy filmmakers at the esteemed showcase for 15 years. More than 60 films from the world over add excitement to the four-day event, starting with the opening night showing and party to the final closing night film—this year, E.T. the Extraterrestrial. The closing night awards ceremony is among the top of Naples’ gala events.

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Oct. 27–29

RedSnook Catch & Release Charity Tournament at Conservancy of Southwest Florida, Naples

Supporting the organization’s mission for clean water, more than 90 anglers participate in guided and non-guided divisions. Although named for two of Southwest Florida’s most popular game fish—redfish and snook—tarpon also figure into the Grand Slam Award, and catfish, ladyfish and jack into the Trash Can Slam.

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Oct. 27–29

Stone Crab Festival at Tin City, Naples

A weekend that is all it’s cracked up to be, it celebrates the opening of stone crab season on Oct. 15 with a party on the waterfront. The hard-shelled stone crab stars, but local seafood of all sorts abound, along with live entertainment and arts and crafts vendors. The festivities start Friday at 5 p.m. with the traditional cracking of the first stone crab claw. Tobacco Rd Band orchestrates the party with country music.

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Oct. 29

Maluma: Don Juan World Tour at Hertz Arena, Estero

With the release of his latest Don Juan album, the charismatic Colombian artist Maluma has set out for 30 North American cities as part of his latest world tour. He’ll debut the album’s latest songs while reprising some of his most popular reggaeton sounds, which consistently top Billboard’s Latin charts.

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Oct. 31 — Nov. 4

John Williams Favorites at Artis-Naples 

Naples Philharmonic Pops pays homage to one of America’s most accomplished modern composers. Memorable scores from blockbuster films such as Jaws, Star Wars, Indiana Jones and Harry Potter are sure to thrill.  

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