Headless Horseman Hussle – Sleepy Hollow, IL 2026
Date
September 20, 2026
Location
Sleepy Hollow, IL
Venue
898 Glen Oak Dr
Start Time
9:00 AM
Entry Fee
$30.00
Events
Headless Horseman Hussle 5k
Includes
T-Shirt
Register NowRegistration Open
Join us for the Headless Horseman Hussle 5K, a fun and energizing community race through the beautiful Village of Sleepy Hollow, Illinois! Whether you're a seasoned runner, a casual jogger, or just want to enjoy a morning walk with friends and family, this event is for everyone. This race is proudly hosted as a fundraiser for the Sleepy Hollow Elementary PTC, with all proceeds going directly towards supporting students, teachers, and school programs in our community. The course will take participants through scenic neighborhood streets making it a perfect event to enjoy the outdoors while giving back. Bring your friends, family, and school spirit as we run, walk, and cheer together for a great cause. Race highlights: 5k run/walk open to all ages and abilities Optional 1k walk for younger participates Community-focused and family-friendly event Proceeds benefit the PTC and local school programs A great way to support education while staying active Come out, get moving, and help make a d
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