Pumpkins in Paradise: Celebrate Autumn in Estero
By Cheryl Mandell
Autumn in Southwest Florida may not arrive with crisp temperatures and hillsides of red and gold, but locals celebrate the season in their own special way. Palm trees share the landscape with pumpkins, scarecrows loom beneath bright, sunny skies and autumn activities rarely require a jacket. October in this area brings everything from outdoor wine tasting and dunk tanks to nighttime nature walks and poolside costume contests.
Ready to celebrate? Check off these eight ways to savor fall in and around Estero this October.
Welcome Fall at the Coconut Point Farmers Market
One sure sign that fall has arrived in Estero is the return of the Coconut Point Farmers Market. The popular Local Roots Farmers Market begins its 2026–27 season on Oct. 1, continuing every Thursday from 9 a.m. to 1 p.m. through April. Shoppers can fill their baskets with fresh produce, seafood, meats, cut flowers, locally harvested honey and baked goods, while also browsing handcrafted soaps, candles, baskets, hats and other artisan finds. Parking is plentiful and free, and the market is pet-friendly. buylocallee.com
Pick the Perfect Pumpkin at Farmer Mike’s
Nothing says fall quite like wandering through a pumpkin patch. Just down the road in Bonita Springs, Farmer Mike’s U-Pick hosts its 12th Annual Fall Festival & Corn Mazes from Sept. 26 through Oct. 31. Families can pick their own pumpkins, sunflowers and wildflowers, then tackle the five-acre, family-friendly corn maze. This year’s maze theme, “The Journey to the Center of the Earth,” includes 16 game stations along the way. Weekend festivities also feature food, drinks, treats and craft vendors, plus a spooky haunted maze for adults and brave older kids. The Family Maze opens Sept. 26, and the Haunted Maze opens Oct. 3. farmermikesupick.com
Meet the Scarecrows at Lakes Park
Throughout October, Lakes Park in Fort Myers transforms into a celebration of old-fashioned fall fun. Scarecrows in the Park and the Fall Festival run Oct. 9-31, with imaginative scarecrows taking over the Children’s Garden. This year’s theme is “Scarecrows at Work.” Families can admire the creations and vote for a People’s Choice favorite during designated voting hours. The Fall Festival brings a huge pumpkin patch, hayrides, inflatables, food and rides aboard the Halloween Express train—plenty of opportunities for those all-important pumpkin-patch family photos. lakespark.org
Explore Corkscrew Swamp Sanctuary After Dark
For a unique outdoor adventure, October offers a different perspective on Southwest Florida nature at Corkscrew Swamp Sanctuary. The Corkscrew Night Tour on Wednesday, Oct. 14 from 7-9:15 p.m. invites visitors to experience the sanctuary when nighttime wildlife take center stage. Enjoy a night in the swamp on this Audubon naturalist-guided walk when the nocturnal animals are out and vocal. A night visit brings the sounds of calling insects, possibly owls and alligators, and perhaps a surprise or two!
This tour is designed for ages 12 to adult and lasts roughly two hours, walking two miles along the boardwalk, with red-light flashlights provided. A shorter Family Night tour for younger children takes place in November. audubon.org/corkscrew
Get Spooky at Estero Park
Costumes, candy and an outdoor family movie make Spooktacular Night at Estero Park a hometown October tradition. Bring all of your little ghouls and goblins to Estero Park on Saturday, Oct. 17, where the fun begins at 5 p.m. with a spirited Trunk-or-Treat. Food trucks and music add to the festivities before families spread out their blankets and lawn chairs for the family movie, “Elio” on the big screen at 7:15 p.m. It’s an easygoing way for little ghosts, superheroes and princesses to safely celebrate the spooky season. leegov.com/parks/centers/estero
Walk for Wishes This Fall
Put on your walking shoes and make one October outing especially meaningful at Walk for Wishes Southwest Florida, taking place Saturday, Oct. 24, at Miromar Outlets in Estero. The family-friendly community event benefits Make-A-Wish Southern Florida and brings together families, friends, coworkers and supporters to help grant life-changing wishes for children with critical illnesses. The event adds purpose to an October filled with pumpkins, costumes and festivals, and serves as a reminder that some of the season’s best family traditions are those that bring the community together for a cause. wish.org/sfla/walk-wishes-southwest-florida
Toast the Season at Hallowine
This annual event is one just for the grown-ups, as Hallowine 2026 takes over Mercato on Thursday, Oct. 29. Presented by the Rotary Club of Naples and Naples Pelican Bay Rotary Club, the Halloween-inspired evening combines curated wine and food tastings from participating Mercato bars and restaurants, along with exciting costume contests and silent auctions with plenty of Halloween spirit. A portion of the proceeds benefits the Warrior Health Foundation, with additional proceeds supporting various Rotary charitable endeavors. VIP admission begins at 5 p.m., with general admission at 6 p.m. naplespelicanbayrotary.com/events
Make a Splash at Big Top Halloween at the Perry Hotel
Celebrate the season with a distinctly Florida twist at The Perry Hotel Naples during its “Big Top Halloween” celebration on Saturday, Oct. 31, from 11 a.m. to 3 p.m. This family-friendly Halloween circus brings the festivities poolside, with pool access, magicians and circus entertainers adding some big-top magic to the afternoon. Guests are encouraged to wear their favorite costumes and bring their swimsuits to enjoy an only-in-Florida combination of Halloween fun, food and splashing in the sunshine. Families looking to settle in for the day can also reserve one of a limited number of daybeds for an additional fee. Search “Perry Hotel Naples” at eventbrite.com.