As summer slips away into fall, Southwest Florida embraces its culture. In Naples, Artis—Naples, The Baker Museum celebrates Florida talent with an art exhibition. In Fort Myers, Florida Gulf Coast University educator Dr. Joel Ying hosts a storytelling session about traditional folklore. And in Cape Coral, the city’s annual Oktoberfest celebrates its 40th anniversary with plenty of fanfare. Don’t miss these October events.
Now — Oct. 26
Farmer Mike’s Fall Festival & Corn Mazes, Lee County
The festival—held weekends at the farm’s Bonita Springs and Fort Myers locations—brings hayrides and pumpkin and sunflower picking. The Bonita flagship farm also has three corn mazes, including a children’s maze, a larger maze suitable for families and a haunted maze for thrill-seekers. Guest food vendors, along with the onsite N’Season Restaurant, serve fresh-squeezed lemonade, milkshakes and farm-fueled bites. Learn More
Now — Nov. 30
Naples Invitational at Naples Art Institute
Held once every two years, this juried group exhibition spotlights around 30 emerging and innovating artists with Naples ties, shortlisted by executive director and chief curator Frank Verpoorten. Works span paintings, sculptures, mixed media and photography, with themes reflecting subjects like environmentalism and identity. Learn More
Now — Dec. 6
Steve Keene: Rauschenberg 100 – A Centennial Celebration at Bob Rauschenberg Gallery at FSW
In honor of the late Captiva Island icon and globally influential artist’s 100th birthday, curator Jade Dellinger commissioned a site-specific installation of 100 paintings from Brooklyn-based artist Steve Keene. TIME has dubbed the prolific artist and Rauschenberg devotee the “Assembly-Line Picasso.” Learn More
Now — Jan. 11
The Way It Looked That Day at Naples Botanical Garden
Photographer John Eder presents a series of new works captured through behind-the-scenes access, homing in on rare blooms, intricate lighting conditions and seasonal shifts. The exhibit offers a meditative exploration of environmental transience and the passage of time. Learn More
Oct. 4
Pink Glow 5K at Founders Square, Babcock Ranch
The evening race sees runners in glowing pink gear navigate a high-visibility route past large lakes, like Babcock and Timber, and the smaller Kinley and James lakes. Open to all ages, the event supports local cancer research initiatives through American Cancer Society of Southwest Florida. Learn More
Oct. 8
Comedian Trish Suhr at Off the Hook Comedy Club, Naples
Trish Suhr, known for her appearances on Clean House and her TV comedy specials, brings sharp, observational humor to Naples. Trish’s style delivers storytelling and relatable lifestyle observations with wit, warmth and plenty of Kentucky-rooted humor. Learn More
Oct. 9 — Nov. 2
Off-Season Art: What Did You Do Over Summer Vacation? at Cape Coral Art League
This loosely themed group show invites artists to reflect on summer in all its forms—whether nostalgic, romantic or filled with the tension of the season’s heat. A variety of media and subject matter, from personal memories to broader reflections on nature, environment and identity, capture the essence of summer. Learn More
Oct. 15 — Nov. 7
Hunt Slonem & Mally Khorasanchi at Harmon-Meek Gallery, Naples
This two-person exhibit features the vivid, layered works of artists Hunt Slonem and Mally Khorasantchi. Hunt’s iconic bunnies and birds juxtapose Mally’s abstract, mixed-media compositions, uniting bold palettes and striking patterns in a dynamic exploration of form and visual rhythm. Learn More
Oct. 15 — Nov. 9
Ada and the Engine at The Naples Players
This historical drama tells the story of Ada Lovelace, often considered the world’s first computer programmer. Set in 19th-century England, the play intertwines biography, romance and scientific innovation, exploring the pioneer’s work with Charles Babbage and her visionary contributions to early computing. Learn More
Oct. 17 — Nov. 20
Girl Feast at Florida Gulf Coast University’s Wasmer Art Gallery, Fort Myers
Artists and FGCU alumnae Izzy Baquerizo and Chloe Lewis present a collaborative exhibit exploring themes of femininity, identity, interpersonal relationships and empowerment. Through a combination of playful illustration, installation and mixed media, the artists address varied interpretations of womanhood, reflecting on both personal and collective experiences. Learn More
Oct. 17
The Vampire Circus at Barbara B. Mann Performing Arts Hall, Fort Myers
A theatrical experience blending circus arts with vampiric folklore, The Vampire Circus embodies the gothic tones of the Halloween season with gravity-defying aerialists, contortionists and dancers performing within a haunted setting. Visual effects like fog machines and strobe lights enhance the otherworldly and darkly entertaining spectacle. Learn More
Oct. 18
Fall Festival at Edison and Ford Winter Estates, Fort Myers
One of the city’s most historic properties transforms with pumpkin patches, craft vendor booths and live music to celebrate the new season. As one of the festival highlights each year, guests brave a climb up the estate’s banyan tree, the largest of its kind in the continental United States. Learn More
Oct. 17-19 and 24-26
Cape Coral Oktoberfest
Perhaps the region’s most raucous iteration on the classic German holiday, Cape Coral Oktoberfest celebrates its 40th anniversary with traditional beer tents, bratwurst, live polka bands and local entertainment. The festival’s host, German American Social Club, encourages attendees to wear traditional attire to complete the experience. Learn More
Oct. 18 — June 28
Florida Contemporary 2025–26 at Artis—Naples, The Baker Museum
Local collage artist Mally Khorasantchi joins with three Florida artists—Boy Kong, Jillian Mayer and Reginald O’Neal—for a dynamic exhibition highlighting some of the most impactful works of the present day. Learn More
Oct. 22
Joel Ying: Folk Tales & Braided Stories at FGCU’s Wasmer Art Gallery, Fort Myers
Physician, educator and storyteller Dr. Joel Ying brings his blend of traditional folklore and personal narrative to the ongoing Storytelling Series. The speaker interlaces classic myths and cultural legends with reflections on identity, healing and community. Learn More
Oct. 23 — Nov. 23
Who’s Afraid of Virginia Woolf? at Gulfshore Playhouse, Naples
The professional theater company is reigniting its macabre side with Edward Albee’s dark comedy. Psychological games and intense, cutting dialogue drive the action as a marriage descends into chaos and painful truths emerge from beneath surface-level facades. Learn More
Oct. 23-26
Naples International Film Festival at Artis—Naples
The annual festival highlights independent cinema, with dozens of films, documentaries and shorts from emerging and established filmmakers. This last night features a screening of 1987 classic The Princess Bride with a live orchestral soundtrack from the Naples Philharmonic. Learn More
Oct. 24 and 25
Nate Edwards Fishing Tournament in Everglades City
Anglers go head-to-head in the waters of Everglades City, battling it out in categories like largest snook, largest redfish and a mystery fish determined by a random hat draw. The event supports local conservation efforts and educational programs. Learn More
Oct. 25
Jordan Davis: Ain’t Enough Road Tour at Hertz Arena, Estero
The country music hitmaker takes to the stage for a high-energy show that highlights his blend of modern country and heartfelt storytelling. Expect chart-topping singles like “Buy Dirt” and “Singles You Up” alongside deep cuts for devoted fans. Learn More
Oct. 28 — Nov. 16
Doubt: A Parable at Florida Repertory Theatre, Fort Myers
The Pulitzer- and Tony-winning play by John Patrick Shanley delves into the complexities of faith, morality and suspicion. Set in a Catholic school in the 1960s, it explores the unsettling tension between a nun and a priest over allegations of misconduct. With no clear answers, the play challenges the audience’s sense of certainty, making for an intense, thought-provoking show. Learn More