Race Discovery
Headless Horseman Hussle
Headless Horseman Hussle logo

Headless Horseman Hussle

Sleepy Hollow, Illinois, United States View on map
Sep 20, 2026 (America/Chicago local time)
Running

About this race

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 difference for our students!

Pick your distance

Running

Headless Horseman Hussle 5k

Sep 20, 2026 5K 9:00 AM
$30.00
Open

Course

Route map and elevation profile

No course map published yet.

The organizer hasn't released a route for this event, and we don't publish guesses. If you're the organizer, send us a GPX file and we'll draw the profile.

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Other races near Sleepy Hollow

Different organizers, within 40 miles, in the next three months

Where this page comes from. Race details were last updated on . We re-check listings regularly and again in the week before race day.

  • Entries, prices, waves and inclusions — the event's official registration page
  • Temperature and humidity — Copernicus ERA5 reanalysis via Open-Meteo (CC BY 4.0)
  • Elevation and terrain relief — Copernicus DEM GLO-90, ESA (CC BY 4.0)
  • Comparisons and counts — Race Discovery calendar, 1 Sleepy Hollow event

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