Looking for Halloween plans that involve a little more dancing and a little less trick-or-treating? Southwest Florida has plenty of ways for adults to celebrate, from downtown bar crawls and rooftop parties to live music, themed cocktails, and costume contests.
With Halloween falling on Saturday, October 31, it’s the perfect excuse to gather your friends, put together a costume, and make a night of it.
Here are some upcoming events around Fort Myers, Bonita Springs, and Naples.
Event details, ticket prices, and availability can change. Check directly with the venue or organizer for current information, age requirements, and reservations before heading out.
Fort Myers Halloween Events
Fort Myers Halloween Bar Crawl
Location: Downtown Fort Myers
Date: Saturday, October 31
Time: 4–10 p.m.; after-party from 10 p.m.–midnight
Admission: Ticketed
Ready to show off your costume around downtown? The Crawl With US Fort Myers Halloween Bar Crawl includes eight participating bars, drink or shot vouchers, and a mid-party at Bay Street Yard.
Check-in is scheduled from 4–6 p.m. at Cowboy-Up Saloon, and guests can visit the participating bars in their preferred order. The night wraps up with an after-party at The Corral.
The organizer lists advance tickets starting at $20 per person for groups of four or more, with individual and door prices varying. crawlwith.us
See bar crawl details and tickets
Halloween Bash at Bay Street Yard
Location: 2136 Bay Street, Fort Myers, FL 33901
Date: Saturday, October 31
Time: Entertainment begins at 5:30 p.m.
Admission: General admission is free
If you’d rather settle in at one spot, Bay Street Yard is throwing a Halloween Bash with music, cocktails, and a costume contest.
DJ Julz is scheduled from 5:30–8:30 p.m., followed by Ian Kelley from 9:30 p.m.–1:30 a.m. The venue also plans Halloween-themed drinks, including nonalcoholic options, and prizes for costume contest winners.
Bay Street Yard has outdoor seating, food trucks, bars, and games, making it an easy place to meet up with friends before exploring downtown. baystreetyard.com
Get the Halloween Bash details
Rooftop Halloween Dance Party at Sidney & Berne Davis Art Center
Location: Sidney & Berne Davis Art Center, Downtown Fort Myers
Date: Saturday, October 31
Admission: Ticketed
Dance under the stars and enjoy views of downtown Fort Myers at the Sidney & Berne Davis Art Center’s rooftop Halloween party. Costumes are encouraged, and the venue is planning a costume contest for guests who want to compete.
The event page lists week-of-event admission at $20. Contact the box office or check the event page for current times, tickets, and contest details before going. www.sbdac.com
View rooftop party information
Bonita Springs Halloween Events
Halloween Monster Mash at Riptide Brewing Company
Location: 28120 Hunters Ridge Boulevard, Bonita Springs
Date: Saturday, October 31
Time: 7–10 p.m.
Admission: No cover listed
Riptide Brewing Company is hosting an adult-oriented Halloween Monster Mash featuring a dance party with DJ Peak Flow, a costume contest, horror movies, and food specials.
It could be a fun choice if you’re looking for a brewery setting and a Halloween party that starts a little earlier in the evening. Check with the venue for the latest event and registration details. playingandlivinginparadise.com
Naples Halloween Events
Halloween 2026 at Seed to Table
Location: 4835 Immokalee Road, Naples, FL
Date: Saturday, October 31
Time: 7:30 p.m.–2 a.m.
Seed to Table is going all out for Halloween with live music, DJs, dancing, drinks, and a costume contest.
Rockadelic is scheduled to perform from 7:30–10:30 p.m., followed by DJ Zee and Scotty D. The costume contest includes individual and couple/group categories, with cash and gift card prizes.
Whether you’re planning an elaborate group costume or just want a lively night out, this one is worth adding to your Halloween list. seedtotablemarket.com
All Hallows Eve Party at The Pub Naples
Location: The Pub Naples, Mercato
Date: Saturday, October 31
Time: DJ entertainment from 8 p.m.–2 a.m.
The Pub Naples is celebrating Halloween with music from DJ 007 and a costume contest offering $1,200 in cash prizes.
If you want to enter the contest, the venue says registration is from 9–11:30 p.m., and participants must be present to win. experiencethepub.com
Halloween at Tipsy Corner
Location: 8855 Immokalee Road, Naples
Date: Saturday, October 31
Time: 8 p.m.–2 a.m.
Tipsy Corner is planning a Halloween night with live bands, DJs, horror movies, and a costume prize. Costumes are encouraged, so this is another opportunity to get creative with your Halloween look.
Check the venue’s event calendar for the latest admission and contest information. tipsycorner.com
See Tipsy Corner’s event calendar
Evening on Fifth: Halloween Edition
Location: Fifth Avenue South, Downtown Naples
Date: Saturday, October 31
Time: 5–8 p.m.
For a more relaxed Halloween outing, head to Fifth Avenue South for an evening of live music along the sidewalks, dining, and shopping.
The event follows the afternoon Halloween Spooktacular at Cambier Park, so you can make a full day of it before enjoying dinner or drinks downtown. www.visitnaplesfl.com
Make a Plan Before You Go
Halloween can be a busy night around Southwest Florida, especially in popular downtown areas and entertainment districts. Before heading out:
- Check tickets and reservations. Some events may sell out or change prices closer to Halloween.
- Bring your ID. Age restrictions vary by event and venue.
- Confirm costume contest rules. Some require registration or have specific entry times.
- Plan your ride home. Choose a designated driver or arrange a rideshare if you plan to drink.
- Check parking and weather. Allow extra time, particularly for outdoor events and downtown celebrations.
Whether you’re in the mood for a bar crawl, a costume contest, or a laid-back evening with friends, there’s no shortage of ways to celebrate Halloween in Southwest Florida. Have fun and stay safe!