Looking for Halloween costume contests in Fort Myers or Cape Coral? Southwest Florida has plenty of opportunities to show off your creativity this Halloween weekend, October 30–31, 2026.
From cash prizes and costume competitions to Halloween bar crawls and rooftop parties, there's something for everyone looking to celebrate the season.
Whether you've spent weeks perfecting your costume or pulled something together at the last minute, here's a roundup of Halloween costume contests and events happening around Southwest Florida.
Please note: The following event details and advertised prizes have not all been independently verified. Confirm dates, times, admission requirements, contest rules, and prizes directly with each venue before attending.
Friday, October 30: Halloween Costume Contests
1. Dixie Roadhouse – Cape Coral
Advertised prizes: $500 for first place, $300 for second place, and $200 for third place
Looking to turn your Halloween costume into some extra spending money? Dixie Roadhouse in Cape Coral is advertising one of the larger individual cash prizes on this list.
Known for its lively nightlife atmosphere, Dixie Roadhouse is a popular destination for dancing and weekend entertainment.
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Location: Cape Coral
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Date: Friday, October 30
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Event starts: 7:00 PM
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Advertised prizes: $1,000 combined for the top three places
If you're going all out with your Halloween look, this could be one to consider.
2. Southern Billiards & Sports Bar – Cape Coral
Advertised prizes: Cash prizes across multiple costume categories
Southern Billiards & Sports Bar is another Cape Coral option for Halloween celebrations.
The advertised costume categories include Most Creative, Sexiest Costume, and Best Couple.
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Location: Cape Coral
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Date: Friday, October 30
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Event starts: 8:00 PM
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Prizes: Cash awards; amounts not confirmed
This could be a fun option for couples planning matching costumes or anyone with a particularly creative Halloween idea.
Saturday, October 31: Halloween Night Events
3. Downtown Fort Myers Halloween Bar Crawl
Advertised prize pool: $2,500 total
Downtown Fort Myers is a popular destination for Halloween nightlife, and the advertised Halloween Bar Crawl brings together participating venues throughout the River District.
The event listing describes a nationwide, multi-city Instagram costume competition with a combined $2,500 prize pool.
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Location: Downtown Fort Myers
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Date: Saturday, October 31
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Starts: 5:00 PM
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Check-in: The Hideaway
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Advertised prize pool: $2,500 across the competition
The advertised prize pool is associated with a multi-city competition and should not be interpreted as $2,500 being awarded exclusively in Fort Myers.
Check ticket details, participating bars, and costume contest rules before purchasing admission.
4. Dave & Buster's – Fort Myers
Advertised grand prize: One year of free video game play
Halloween isn't just about cash prizes. Dave & Buster's at Bell Tower in Fort Myers is listed as hosting a Halloween celebration featuring a costume contest and a gaming-related grand prize.
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Location: Bell Tower, Fort Myers
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Date: Saturday, October 31
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Time: 7:00 PM–10:00 PM
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Advertised prize: One year of free video game play
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Admission: Ticket required according to the event listing
Confirm the restrictions and actual value of the gaming prize with the venue.
5. Backyard Social – Fort Myers
Advertised prizes: Cash awards across multiple categories
Backyard Social is listed as hosting an Asylum After Dark Halloween celebration, combining music, costumes, and entertainment.
The advertised event includes three costume contest categories with cash prizes.
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Location: Fort Myers
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Date: Saturday, October 31
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Starts: 6:00 PM
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Prizes: Cash awards; amounts not confirmed
For anyone who loves an energetic outdoor atmosphere, this could be a fun way to spend Halloween night.
6. Bay Street Yard – Downtown Fort Myers
Advertised prizes: Gift cards and Halloween merchandise
Bay Street Yard offers another Halloween nightlife option in the Downtown Fort Myers River District.
The advertised event includes costume festivities and giveaways in its outdoor courtyard setting.
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Location: Downtown Fort Myers
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Date: Saturday, October 31
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Listed hours: 5:00 PM–1:30 AM
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Advertised prizes: Gift cards and Halloween merchandise
It's an option worth checking for anyone planning to spend Halloween downtown.
7. Chocolattés – Fort Myers
Advertised prizes: Local prizes and café treats
Looking for something a little different?
Chocolattés on San Carlos Boulevard is listed as hosting a celebrity-themed costume competition with live local music.
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Location: San Carlos Boulevard, Fort Myers
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Date: Halloween weekend; exact date unconfirmed
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Theme: Dress Like a Celebrity
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Advertised prizes: Local prizes and café treats
This could be a fun choice for anyone who prefers a themed costume party over a traditional nightclub event.
8. Sidney & Berne Davis Art Center – Downtown Fort Myers
Advertised prizes: Trophy and rooftop perks
For a Halloween celebration with a downtown view, the Sidney & Berne Davis Art Center is listed as hosting a Rooftop Halloween Dance Party.
The event information describes costume voting and Halloween entertainment.
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Location: Downtown Fort Myers
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Date: Saturday, October 31
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Time: 8:00 PM–12:00 AM
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Advertised prizes: Trophy and rooftop perks
Check the venue's official event calendar for admission information and confirmation of any costume competition.
Which Southwest Florida Halloween Costume Contest Has the Biggest Prize?
If you're choosing your Halloween destination based on prizes, here's a quick comparison.
| Event | Advertised Prize |
|---|---|
| Downtown Fort Myers Bar Crawl | $2,500 multi-city total pool |
| Dixie Roadhouse | $500 first-place cash prize |
| Southern Billiards | Cash prizes; amounts unspecified |
| Backyard Social | Cash prizes; amounts unspecified |
| Dave & Buster's | One year of free game play |
| Bay Street Yard | Gift cards and merchandise |
| Chocolattés | Local prizes and café treats |
| Sidney & Berne Davis Art Center | Trophy and rooftop perks |
For a clearly stated individual cash award, Dixie Roadhouse stands out with its advertised $500 first-place prize. The Downtown Fort Myers Bar Crawl lists a larger overall prize pool, but it spans multiple cities.
Because some venues haven't published confirmed prize amounts, this isn't a definitive ranking of every contest's payout.
Celebrate Halloween in Southwest Florida
Halloween weekend is a great opportunity to explore local businesses, support Southwest Florida entertainment venues, and enjoy a night out with friends.
Whether you're celebrating in Cape Coral, heading to Downtown Fort Myers, or looking for a themed party closer to home, there are plenty of possibilities for Halloween fun.
Before you go: Always check each venue's official website or social media pages for the latest information. Costume contests may have registration deadlines, age restrictions, cover charges, or specific judging times.