Headless Horseman Hussle
Headless Horseman Hussle is a running race on September 20, 2026 in Sleepy Hollow, IL, with an entry fee of $30.
- Date
- September 20, 2026 (59 days to go)
- Price
- $30
- Sport
- Running
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!
Events
Weather
Typical Conditions
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
74°
Typical Low
51°
Chance of Rain
32%
Based on US Climate Normals data from Elgin, 2 mi from the venue.
Host City
About Sleepy Hollow, IL
Nearest Airport
ORD
Chicago O'Hare International Airport · 21 mi
Time Zone
Central Time
From Endurance Grid
Line up lodging and travel early to lock in your race weekend.
Race Location
Your Next Start Line
What Are You
Waiting For?
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.
59
Days to train
- Race
- Headless Horseman Hussle
- Date
- September 20, 2026
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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 an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Coming Up
More Running races near Sleepy Hollow, IL
RUN FOR C'VILLE
2 Mile / 3K · 5K · From $45 · 300 Carpenter Blvd
1 mile away
Go Fish 5K & Kids' Color Run
1 Mile · 5K · From $15 · 310 E. Main Street.
Less than a mile away
Heritage Fest 10k
5K · 10K · From $25 · 117 S. First St.
Less than a mile away
Still Standing
1 Mile · 5K · From $15 · 270 N. Grove Ave. Elgin, IL 60120
4 miles away
Plan your trip
Make it a Racecation
Coming from out of town? There's more to Sleepy Hollow than race day. We'll help you line up nearby lodging, flights, a rental car, and things to do so you can make the most of your racecation.
Plan your trip to Sleepy HollowFrequently Asked Questions (FAQs)
What is the Headless Horseman Hussle?+
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Headless Horseman Hussle
Sep 20, 2026