Get Spooky on the Sun Coast: Halloween Guide to Sarasota & Siesta Key
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 Official 2025 Halloween Event Lineup (Sarasota & Siesta Key)
Based on the latest local listings, here are the specific must-do events happening during your Siesta Key vacation this year:
Island & Village Fun (Siesta Key Specific)
| Event | Date & Time | Location | Description |
| Siesta Key Safe Treats | Friday, Oct. 31 (3:00 PM – 6:00 PM) | Siesta Key Village | A free, safe trick-or-treating event where kids can collect candy from participating local businesses displaying festive balloons. |
| Siesta Key Scarecrow Stroll | Oct. 1 – Oct. 31 (All Month) | Siesta Key Village & Area | Enjoy walking or driving around the island to see creative, homemade scarecrow displays decorating storefronts. Vote for your favorite! |
| Candlelight: A Haunted Evening | Saturday, Oct. 25 | Siesta Key (Specific venue varies) |
Family Fun & Fall Festivals
These events in the Sarasota area offer safe, daytime fun for all ages:
| Event | Date & Time | Location | Description |
| Lights at Spooky Point | Oct. 3 – Nov. 1 (6:30 PM – 9:00 PM) | Historic Spanish Point (Selby Gardens) | Follow an eerily lit path through the woods featuring fantastical creatures and light designs, designed for all ages. |
| 37th Annual Fruitville Grove Pumpkin Fest | Weekends in October (Starting Oct. 4) | Fruitville Grove Farm | A massive fall festival featuring hayrides, pony rides, the Hollowgraves Haunted Manor walk-through, circus acts, and a costume contest every Saturday at 2 p.m. |
| Goblin Gathering | Friday, Oct. 17 | GT Bray Park, Bradenton | A large, free, and family-friendly outdoor event with candy, games, costume contests, and activities. |
| Boo Bash: Trick-or- Treat on the Lake | Tuesday, Oct. 28 (5:30 PM – 8:00 PM) | Nathan Benderson Park | A free family event where vendors line Regatta Island for trick-or-treating, plus interactive activities, storytelling, and live music. |
| Fright Night on St Armands Circle | Friday, Oct. 31 (Time varies) | St. Armands Circle | The Circle is transformed for this popular annual event, featuring trick-or-treating at local shops and restaurants, decorated storefronts, and costumed characters. |
Adult Thrills & Spooky Adventures
For the 18+ and 21+ crowds looking for some extra fright or festivity:
| Event | Date & Time | Location | Description |
| Sarasota Haunted History Tours | Oct. 1 – Oct. 31 (Select Nights) | Downtown Sarasota / Anna Maria Island | Choose from guided walking or trolley tours that delve into Sarasota’s haunted past, complete with ghost stories and tales of mayhem. |
| Witches Night Out | Friday, Oct. 10 | Edson Keith Mansion, Phillippi Estate Park | A bewitching evening for adults featuring a live DJ, shopping with unique vendors, a cash bar, a photo booth, and a costume contest for the best witch or wizard attire. |
| Sarasota Boos & Booze Bar Crawl | Saturday, Oct. 25 | Downtown Sarasota | Put on your best costume and join this pub crawl through downtown hot spots for drink specials, two complimentary shots, and a cash prize costume contest. |
| Clasico Day of the Dead Block Party | Saturday, Nov. 1 (2:00 PM – Midnight) | Main Street, Downtown Sarasota |
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,
