Grown Ups! Join Wekiva Island for a scary good time at their Halloween Costume Contest & Party

 The adult costume contest is 21+ with some seriously big prizes up for grabs, including $500 cash and a $500 Wekiva Island gift card for Wekiva’s Wickedest!

Dark, silent water. Clouds drifting across the moon. The wind blowing through the Spanish moss. Things are getting downright spooky at Wekiva Island, and this wekend things are sure getting a little wicked after dark...

When the sun goes down over the Wekiva River, the little ghosts and goblins go home…and the grown-up monsters come out to play.

Join Wekiva Island located at 1014 Miami Springs Drive, Longwood for the Wekiva Island Halloween Party & Costume Contest on Saturday, October 24, 2026.

The night features live music by Atlantic Alibi, cold drinks, dancing, riverside Halloween mischief and some seriously big prizes for those willing to bring their costume A-game.

The party takes over the Island from 7–11 pm, with the Costume Contest Line-Up at 8 pm.

And thee’re not handing out fun-size candy bars for prizes…

WEKIVA’S WICKEDEST - $500 CASH + $500 Wekiva Island Gift Card

1st Place - $300 Cash + $200 Wekiva Island Gift Card

2nd Place - $250 Cash + $100 Wekiva Island Gift Card

3rd Place- $150 Cash + $50 Wekiva Island Gift Card

BEST GROUP COSTUME - A Beach Club Rental + Cabana Feast for up to 20 guests!

Orlando Halloween Events Guide 2026 with Frightful Fun for Everyone!

This adults-only event is free to attend. Come creepy. Come clever. Come completely ridiculous. Come as something that makes us wonder how you drove here wearing it.

Just don’t come in a costume you threw together five minutes before leaving the house and expect to walk away Wekiva’s Wickedest. The competition is real, and so are the prizes.

Grab your crew, unleash your alter ego and get ready for a Halloween night of music, costumes, cocktails and mischief on the Wekiva River. The swamp gets a whole lot wilder after dark.

For more information: https://wekivaisland.com/event/halloween-costume-contest-party/

To cap off the month of fun, Paddleboard Orlando will have its annual Halloween Costume Parade Paddle on Oct. 31. Launch begins at 10:30 a.m., with judges in front of Wekiva Island from 10:30 to 11:15 a.m. The event is free to those who bring their own boards, with rentals available.

All the fun is in addition to another new addition to Wekiva Island—The Cypress Cove Coven pop-up cabana. This popular rental space will be decked out with floating candles, spell books, spooky lighting and more to bring a true Halloween vibe from Oct. 1-31. For more information or to book, click here.

For more information about any of Wekiva Island’s October events, visit https://wekivaisland.com/halloween/. 

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