As the Gulf waters remain blissfully inviting and the sea breeze carries a hint of crispness, Southwest Florida leans into its own version of autumn. October here isn’t about leaf piles or sweaters (well, not quite)—it’s about festivals in the golden light and community gatherings under sugar-maple skies (or the Florida equivalent: palm fronds turning bronze in sunset glow).
This month, you’ll find Oktoberfests echoing with accordion and laughter, scarecrow art popping up in parks, haunted trails lighting the night, and riverside estates transforming into festive playgrounds. Families bundle around pumpkin patches and craft booths; music drifts from stage to street corners; and the calendar swells with ways to welcome cozy season vibes in our tropical terrain.
So pour yourself something spiced (iced or hot, your call), pick your favorite hat (witchy, wide-brimmed, cowboy — fall is inclusive), and let’s explore what’s happening this October across Fort Myers, Cape Coral, Naples, and the stretch in between.
🍁 October 2025 Event Roundup
Here’s a curated list of festivals, concerts, family fun, and spooky delights happening this October around Southwest Florida. (Always double-check with organizers — things shift in paradise.)
| Date(s) | Event | Location | Highlights / Notes |
|---|---|---|---|
| Fri-Sun All Oct | 11th Annual Fall Festival | Farmer Mike's Bonita | The Lost City of Atlantis Family Friendly 5 Acre MAZE, Haunted Corn Maze, Fun Hay Maze, Pick your own pumpkin, Axe Throwing, Bounce House and More! |
| Every Tues | Ladies Night at Next Door | Next Door, Cape Coral | Enjoy girls night out with great food: Starter, Main, Dessert, One Glass of Wine for $38 |
| Oct 1 | Hot Girl Walk | Centennial Park | Her Table Meet Up Group. End with a cocktail at Bay Street Yard |
| Oct 1 | Sunset Fest | Four Freedoms Park | We will have great vendors, food trucks, live music and a beautiful sunset! Free Family Community Event: Free entrance and parking. |
| Oct 3 |
TSwift Album Release Party | Moonflower Market, Cape Coral | 8pm. Exclusive Charm Bar Drop. Hang out with the girlies at Moonflower! |
| Oct 3 | Candle Making Workshop (Various Dates) | Wallflower Cafe, Cape Coral | Make your own candles! |
| Oct 3 | Azalea's Art Walk Pop-Up | Common Grounds, Downtown Ft Myers | Feat. Artist Marie Dyer at Common Grounds Pocket Park across from Ford's Garage. Starts at 5pm |
| Oct 3 | Freaky Friday | Velvet Crush Aesthetic Lab, Cape Coral | Spooky swag bags, raffles, mega discounted services, drinks and snacks. 11am-6pm |
| Oct 3–5 |
9th Annual Millennial Oktoberfest | Fort Myers (Millennial Brewing Co.) | German food, beer, Bavarian performances, contests. Free entry & parking. |
| Oct 4 | Kiwanis Kid Fest | 544 Cultural Park Blvd, CC | Live Music, Food Trucks, Venders, Stge Shows, Giveaways, Costume Contest 10am-3pm |
| Oct 4 | Glow Party Paddle | Lovers Key, Ft. Myers Beach | A night out on the water with paddles and boats covered in glow sticks 8pm |
| Oct 4 | The Cypress Coffee House Grand Opening | 8400 Cypress Lake Dr, Fort Myers | The cutest coffee shop is opening! Go support them. |
| Oct 4 | Bestie I'm Booked | Moonflower Market, Cape Coral | Books, Coffee, and Tarot Card readings 2-5pm |
| Oct 4-5 | Bones & Bales Fall Festival | Gater Mikes Family Fun Park, CC | 12pm-6pm |
| Oct 10 | Halloween Zappy Hour Girls Night: Moon & Metal Collab | 1490 Pine Island Rd., Unit 5A Cape Coral | Permanent jewelry, cocktails, tshirts, tooth gems, and teeth whitening |
| Oct 10-30 | Lakes Park Fall Festival – “Scarecrows in the Park” | Lakes Regional Park, Fort Myers | Pumpkin patch, bounce houses, hayrides, Halloween Express train, scarecrow displays. |
| Oct 10-30 |
Halloween Express Train Ride | Lakes Regional Park, Fort Myers | Tickets $6 per rider Ages 6+ |
| Oct 11 | Charmed Event | Moonflower Market | Spooky Edition of your favorite charm scavenger hunt around Cape Coral. 10am-4pm. |
| Oct 16 | Wine Glass Painting Class | Barunch, Cape Coral |
Wildly Wicket Witch wine glass painting class at 6pm. $20/person |
| Oct 16 | Sip and Paint | Rooftop at Riverside, Bonita Springs |
$35 for two pumpkins and two glasses of house wine. Live DJ from 6-9pm |
| Oct 17 | Haunting Hour at the Wallflower | 1615 SE 47th Ter, Cape Coral |
Spooky Mocktails, Baked goods, costume party 6:30pm-9:30pm |
| Oct 17 | Boo-Tacular | 15000 Livinston Road, Naples |
Haunted Trail, Trick or Treat Lane, Food Trucks, DJ, Bounce Houses, Games, Crafts, Caricature Artist, Photo Booth, Dunk Tank and more! |
| Oct 17 | Boots N Beats | The Ranch Concert Hall & Saloon | A night of live country music & EDM DJ set. |
| Oct 17–19 & 24–26 | Cape Coral Oktoberfest (40th Annual) | German-American Social Club, Cape Coral | Two weekends of German food, live music, dancing, carnival area, vendors. |
| Oct 18 | Pumpkins and Pilates | Yoga House Naples | Kick things off with a Hot Pilates class led by @oliviaguzzo 🔥 then explore our wellness market featuring local vendors, live DJ @paige.noir , cozy fall vibes, pumpkin painting + more. |
| Oct 18 | South Cape Spooktacular Pub Crawl | Big John's Plaza | Join us for a fang-tastic Halloween Pub Crawl on October 18 from 7-11 PM, and sip on wicked drink samples while munching on sweet candy treats at South Cape’s spookiest hotspots! |
| Oct 18 | Spooktacular Night | Estero Park | Enjoy a Trunk or Treat in the park starting at 5pm. Then move to the large event field behind the center to enjoy a Movie in the Park: A Minecraft movie (rated PG). |
| Oct 18 | Edison & Ford Winter Estates Fall Festival | Fort Myers | Craft vendors, food & drink, pumpkin picking, riverside activities. |
| Oct 18 | Tropical Plant Sale | Rotary Park, Cape Coral | 9am-2pm Orchids, bromeliads, butterfly plants, tropical hibiscus, pottery and more |
| Oct 19 | Pumpkins and Plants | M&M Farms | Fall in love with succulents! Design your own pumpkin arrangement with real plants—perfect for cozy seasonal décor. |
| Oct 23-31 | Happy Haunts Immersive Halloween Stroll | Downtown Bonita Springs | 7-10pm |
| Oct 24 – Nov 12 | NIFF (Naples International Film Festival) | Naples | Multi-day film fest, opening/closing galas & screenings. |
| Oct 24 | Fright Night | Bay Oaks Park, Fort Myers Beach | Costume contest, music, inflatables, candy, Halloween fun. |
| Oct 24 | Monster Mash Bash | Veterans Park & Recreation Center, Lehigh Acres | Little Ghouls and goblins can explore a trick or treat trail, music and games during this free family-friendly event! |
| Oct 24 |
Family Fall Festival | North Fort Myers Park | Gourds, ghouls, and good times at this free family events for all ages. Games, candy, music, photo booth and costume contest. |
| Oct 25 | Padgett Ranch Family Fest | 5422 NE McIntyre St., Arcadia, FL | Fun for the whole family! |
| Oct 26 | Fall Festival | Edison & Ford Winter Estates | Enjoy some fall things with us as you stroll along and shop craft vendor booths, get something to eat and drink and listen to music. Plus, there will be fun activities! |
| Oct 27–29 | Stone Crab Festival | Tin City, Naples | Local seafood, arts, music, waterfront celebration. |
| Oct 27–29 | RedSnook Catch & Release Charity Tournament | Naples / Conservancy of SW Florida | Sport fishing fundraiser supporting clean water initiatives. |
| Oct 25 – Nov 20 | Rush of Color exhibit | Bonita Springs | Juried art show across many media. |
| Oct 21 | Taste of North Port / Fall Festival | North Port (City Hall Center Green) | Food trucks, crafts, costume parade. |
| Oct 27–29 | Ranchettes Fall Festival | Punta Gorda area | Pumpkin patch, hayrides, petting zoo, food trucks & games. |
| Oct 28 | Engage Estero Community & Member Meeting | Estero Rec Center | Public community meeting covering local development, HOAs, infrastructure. |
| Oct 30 | Coffee + Beats- CIRQUE DU MOONFLOWER Halloween Party | Moonflower Market, Cape Coral | 8-11pm. Coffee and a great DJ |
and more around the edges:
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Fort Myers Fairs & Festivals series — keep an eye on rotating events, markets, and concerts.
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La Mesa RV / Florida Gun Show / Greater Naples Dog Club Show — occasional events at Lee County Civic Center.
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Fright Night, special beach events & nights along Fort Myers Beach & surrounding towns.
🍂 Tips for October in SWFL
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Fall (Florida style) doesn’t mean chilly — days still hover warm; evenings may carry a soft breeze. Dress in layers.
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Because we’re subtropical, don’t expect blazing leaf color, but local decor, pumpkins, scarecrows, and ambient lighting bring that autumn feel.
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Weekends will be packed — get tickets early for film fests or popular festivals (Oktoberfest, NIFF).
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Mix big & small — join the marquee events and discover local trunk-or-treats, art walks, and community gatherings.
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Check for updates — hurricane season sometimes lurks late into October; weather can shift plans.
