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 - SRQ, FL
5.0  5 Rating (1)
1548 Main St., Sarasota FL, 34236
Join the Costumes & Cocktails Witching Hour (Realtors Event) at Cask and Ale on the 26th of October in your favorite Halloween attire!
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!
The Gator Club
5.0  5 Rating (1)
1490 Main St, Sarasota FL, 34236
The Gator Club's annual Halloween Block Party will feature live band performances by Johnny Diamond and Dj Kelly Crawford. It is the ideal location for participating in the costume contest and winning cash and prizes. Additionally, food trucks are also available. The party is from Oct 29, 6:00 PM to Oct 30, 2:00 AM.
GT Bray Park
Recreation $
5502 33rd Avenue Drive West, Bradenton FL, 34209
GT Bray Park is again organizing the grand outdoor Goblin Gathering family event. As per custom, they are also focusing on Halloween costume contests.
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.
Sage SRQ
4.4  5 Rating (1)
1216 First Street, Sarasota FL, 34236
The ancient Sarasota Times building will once again be recreated into a spooky house to honor its seductive past filled with spectral beings and demonic manifestations.
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

on Saturday, 29 Oct, 2022 9:00 AM
at Sarasota Farmers Market
Lemon & Main, Sarasota, FL 34236
Attending Interested

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

on Friday, 1 Nov, 2019 8:00 AM
at Turtle Bay Lounge
3601 14th St W, Bradenton, FL 34205
Attending Interested

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

on Thursday, 31 Oct, 2019 11:00 PM
at Daiquiri Deck | Siesta Key Village
5250 Ocean Blvd, Siesta Key, FL 34242
Attending Interested

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

on Tuesday, 29 Oct, 2019 5:30 PM
at Arlington Park & Aquatic Complex
2650 Waldemere St, Sarasota, FL 34239
Attending Interested

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

on Thursday, 26 Oct, 2017 6:00 PM
at South Manatee Branch Library
6081 26th St W, Bradenton, FL 34207
Attending Interested

Join us for Spooky Family Storytime with Trick-Or-Treating