Halloween is simply the best time of year! This beautiful fall holiday isn’t just about trick-or-treating or ghoulish decorations - it is also an opportunity to dress up as your favorite character, go out, and play — and we guess this is exactly what you want to do in Sarasota this Halloween.
If you are looking for a place to go dressed up, we’ve got you. There are several spots in Sarasota where you can party and stand a chance to win a prize for your awesome costume! So, for all the spooky fun, no further than these places in Sarasota.
Related Read: Best Haunted Houses in Sarasota and Bradenton this Halloween

Cask Ale and Kitchen is a restaurant located on Main Street, Sarasota. The place is known for offering an eclectic menu of delicious cuisine. They also have a fun atmosphere that encourages you to come in costume and enjoy delicious food!
This Halloween, visit this popular spot to enjoy the costume contest, spooky cocktails, refreshments, and surprising prizes!


A costume contest will be held for the following age groups: infants and toddlers, children aged 2 to 4, children aged 5 to 8, children aged nine and above, and families. Each category will have three winners. Anyone interested in participating can sign up at the stage between 5:30 and 6:15 PM. Onstage judging begins at 6:30 PM.

Here, unique costumes are appreciated and rewarded! There is a fun costume competition in the evening that brings life to the event.
They will also provide free spooky canapés and mouthwatering haunted hors d'oeuvres for the ghouls and visitors! Do not forget to check the mansion mixologists' spookiest concoctions, these will be available at the cash bar.
Sarasota DOG-A-WEEN Costume Contest
at Sarasota Farmers Market
Treat your Lovely pet dogs and Dress them up with the Best Halloween Costume to have an amazing time with us @ Sarasota Farmers Market for our Sarasota DOG-A-WEEN Costume Contest!

Halloween Costume Contest
at Turtle Bay Lounge
Cash prizes for 1st pl 2nd pl 3rd pl food live karaoke must be signed in for contest by 10pm side dishes welcome
Hall-O-Ween Costume Contest
at Daiquiri Deck | Siesta Key Village
Join us at Daiquiri Deck Siesta Key Village this Hall-o-ween for a costume contest with cash prizes! Enjoy trick-or-treating with your little ones and then come in costume for a chance to win $100!
Bark-O-Ween Dog Costume Contest
at Arlington Park & Aquatic Complex
Back by popular demand is the Bark-O-Ween Dog Costume Contest! Dress up your dog and walk in the judged costume parade for a chance to win prizes!

Spooky Family Storytime with Trick-Or-Treating & Costume Contest
at South Manatee Branch Library
Join us for Spooky Family Storytime with Trick-Or-Treating
