Get Spooky on the Sun Coast: Halloween Guide to Sarasota & Siesta Key
This Halloween guide to Sarasota & Siesta Key lists 12 events confirmed for October 2026, from free trick or treating in Siesta Key Village on Saturday, October 31 to the 38th annual Fruitville Grove Pumpkin Festival every weekend through November 1. Most are free or low cost and sit within a short drive of the island.
Siesta Key’s Spooktacular Side: Decorations & Delights
One of the best parts of a Halloween Siesta Key vacation is seeing the island transform. Our local businesses and residents go all-out with decorations, creating a festive backdrop perfect for sunset strolls and costume photos!
Here are a few glimpses of the kind of Halloween magic you can expect to see on Siesta Key:
A festive entrance to a Siesta Key home, adorned with pumpkins and friendly ghosts.
Palm trees on Siesta Key wrapped in purple and orange lights, with spiderwebs draped between them.
Your 2026 Halloween Event Lineup in Sarasota & Siesta Key
Here are the events confirmed for October 2026 during your Siesta Key vacation. Every date below was checked against the organizer, the county, or a local news listing on October 2, 2026. Halloween falls on a Saturday this year, so several of the biggest events land on the same evening.
Island & Village Fun on Siesta Key
| Event | Date & Time | Location | Description |
| Siesta Key Safe Treats | Saturday, Oct. 31 (4:00 PM to 6:00 PM) | Siesta Key Village | A free, safe trick or treating event where kids collect candy from participating local businesses. |
| Siesta Key Scarecrow Stroll | Oct. 1 to Oct. 31 (All Month) | Siesta Key Village storefronts | Walk the Village to see handmade scarecrow displays decorating local businesses. |
| Candlelight: A Haunted Evening of Halloween Classics | Saturday, Oct. 24 (6:15 PM) | St. Boniface Episcopal Church, 5615 Midnight Pass Rd, Siesta Key | Halloween and scary movie classics performed by a live string quartet, surrounded by candlelight. Ticketed, ages 8 and up. |
Planning the kids’ route for Halloween night? Our guide to the best places to trick or treat in Siesta Key covers where to go once Safe Treats wraps up.
Family Fun & Fall Festivals Near Siesta Key
These events in the Sarasota area offer safe, family friendly fun for all ages:
| Event | Date & Time | Location | Description |
| Lights at Spooky Point | Oct. 1 to Oct. 31 (timed entry at 6:30 PM and 7:45 PM) | Selby Gardens Historic Spanish Point, Osprey | An eerily lit woodland path with fantastical creatures and light designs, now in its fifth season. The 6:30 PM slot suits younger kids. |
| 38th Annual Fruitville Grove Pumpkin Festival | Saturdays and Sundays, Oct. 3 to Nov. 1 (10:00 AM to 5:00 PM) | Fruitville Grove, 7410 Fruitville Rd, Sarasota | A classic fall festival with pumpkins, rides, and family activities. $5 admission and free parking. |
| Goblin Gathering | Friday, Oct. 16 (4:00 PM to 7:00 PM) | GT Bray Park, Bradenton | A free outdoor event with candy, games, and a costume contest, run by Manatee County. |
| Trick or Treat on the Lake | Tuesday, Oct. 27 (4:30 PM to 7:30 PM) | Regatta Island, Nathan Benderson Park | A free family event where vendors line Regatta Island for trick or treating. |
| Boo! at The Bay | Saturday, Oct. 17 (5:00 PM to 7:45 PM) | The Bay Park, Sarasota | A family movie night on the bayfront. |
| Fright Night on St. Armands Circle | Saturday, Oct. 31 (5:30 PM to 8:00 PM) | St. Armands Circle | The 18th annual merchant hosted night of trick or treating at local shops and restaurants. |
| Halloween at The Ringling | Saturday, Oct. 31 (4:00 PM to 7:00 PM) | The Ringling, 5401 Bay Shore Rd, Sarasota | Free trick or treating and art making on the museum grounds. |
Adult Thrills & Spooky Adventures
For the 12+ and 21+ crowds looking for some extra fright or festivity:
| Event | Date & Time | Location | Description |
| Haunted Sarasota Trolley Tour | Nightly in October (7:00 PM) | Departs 1826 4th St, Downtown Sarasota | A guided trolley tour through Sarasota’s haunted past and ghost stories. Ages 12 and up. |
| Sarasota Boos & Booze Halloween Bar Crawl | Saturday, Oct. 31 (3:00 PM to 10:00 PM) | Starts at Raffurty’s, 1888 Main St, Downtown Sarasota | A costumed pub crawl through downtown bars with drink specials and a costume contest. 21 and over. |
Whether you’re hunting for ghosts, competing for the best costume, or just filling up on candy in Siesta Key Village, your Halloween Siesta Key vacation is guaranteed to be a hit. Get your plans finalized and your costumes ready—Sarasota is waiting to greet you with a friendly, spooky smile! Happy Haunting,
