Headless Horseman Hussle
- Date
- September 20, 2026
- Distance
- Headless Horseman Hussle 5k
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:
- 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!
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104
Days to train
- Race
- Headless Horseman Hussle
- Date
- September 20, 2026
Coming Up
More Running races in Illinois
From Endurance Grid
About This Sport
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.
Running
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)
- What is the Headless Horseman Hussle?
- Headless Horseman Hussle is a running race held in Sleepy Hollow, Illinois on September 20, 2026. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more running races near you or explore our sports guides to learn what race day actually feels like.
- When and where is the Headless Horseman Hussle?
- Sunday, September 20, 2026 in Sleepy Hollow, Illinois at 898 Glen Oak Dr, Sleepy Hollow, IL. Check the event page for exact start times and wave schedules.
- How do I register for the Headless Horseman Hussle?
- Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.
Headless Horseman Hussle
Sep 20, 2026