898 Glen Oak Dr, Sleepy Hollow IL
Sunday, September 20th, 2026
Event Overview
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.
Fundraising Details
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.
Course Information
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
- Event Type: 5k run/walk open to all ages and abilities
- Optional Distance: Optional 1k walk for younger participants
- Community Focus: Community-focused and family-friendly event
- Proceeds: Proceeds benefit the PTC and local school programs
- Active Support: A great way to support education while staying active
Call to Action
Come out, get moving, and help make a difference for our students!
Event Details
Date: 2026-09-20
Location: 898 Glen Oak Dr, Sleepy Hollow, IL
Registration Link: Sign Up Here
Race-day essentials
Light, simple picks for a fast effort.
Top pick
SHOKZ OpenRun Bone Conduction Open-Ear Bluetooth Sport Headphones, Running Workout Bundle with Waterproof Carrying Case & Sweat Headband, IP67 Sweat Resistant, 8H Playtime, Mic, Black
$129.95
Garmin Forerunner 55, GPS Running Watch with Daily Suggested Workouts, Up to 2 Weeks of Battery Life, Black - 010-02562-00
$164.99
goodr A Unicorn's Calamity Polarized Sunglasses, Medium Sized (OG), Black Solid Frames with Black Non-Reflective Glare Reducing Lenses, UV400 Protection, No Slip, No Bounce
$30.00
Nathan Peak Running Hydration Waist Pack Belt w/Speed Draw Flask Water Bottle, 18oz/535 ml Push/Pull Race Cap, Expandable Zippered Stretch Pocket
$44.00
Course Map
Train for this race
Find a local run club
Run clubs in Sleepy Hollow, IL host weekly group runs — a great way to prep for race day.
