This town blends its small-town charm with just a slight touch of spooky fun, especially in the fall. The village’s annual “Halloween in the Hollow” celebration features a chili cookoff competition, costume contests for all ages, hayrides, pumpkin decorating, food and drinks, and a community bonfire. The highlight? A special appearance by the legendary Headless Horseman himself.
Sleepy Hollow is participating in Explore Elgin Area’s Stick and Stay Trail to celebrate serving the Elgin area for 40 years. This program allows you to win prizes when you collect 12 stickers from one of the 24 destinations participating in the program. Collect these stickers in person or digitally when you visit the attractions and submit them to the Explore Elgin Area Visitors Center to redeem your prize (as long as supplies last).
Join The Trail
To join the Stick & Stay Trail, claim your stamp through our Trail App or pick up a physical passport and destination sticker:
Main Desk at the Sleepy Hollow Village Hall located at 1 Thorobred Ln., Sleepy Hollow.
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