
From the Organizer
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:
Come out, get moving, and help make a difference for our students!
Events
Race Location
Your Next Start Line
Every finish line starts with a single decision. Claim your spot at Headless Horseman Hussle, put it on the calendar, and turn “someday” into a start date.
104
Days to train
Coming Up
From Endurance Grid
Endurance Grid is here to help you understand the sport, decide if it's the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer's event page.
With running, there's a distance for every fitness level, a community at every start line, and nothing beats the feeling of crossing a finish line you trained for.
Running is an endurance sport that rewards consistency, and showing up every week compounds in ways that will surprise you.
From 5K to marathon, running races are the most accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Frequently Asked Questions (FAQs)
Headless Horseman Hussle
Sep 20, 2026