In 5 days · Sun, Sep 20, 2026
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Sunday, September 20th, 2026
898 Glen Oak Dr, Sleepy Hollow IL
5K
60–77°F · some rain risk
See last 10 years
On this date: rain 3 of the last 10 years
2025
61–79°F
rain
2024
68–86°F
dry
2023
60–77°F
dry
2022
61–88°F
rain
2021
68–80°F
rain
2020
47–69°F
dry
2019
66–83°F
dry
2018
64–86°F
dry
2017
64–88°F
dry
2016
65–80°F
dry
Best months to race in Illinois →
Race-day forecast · Sunday, Sep 20
Rain likely · 67–75°F
Sunday, Sep 20starts near 67°F · 43% chance of rain · wind up to 12 mph
About this race
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
Course map
Hotels for race weekend
Live prices near the start line, Sep 19 – 21, 2026.
Train with a club
Run clubs near Sleepy Hollow to train with before race day.
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