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Headless Horseman Hussle

location_on

Sleepy Hollow, Illinois, United States

calendar_today 20 Sep, 2026

directions_run Running

sell $30.00

About the Event

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!

Races Offered

Headless Horseman Hussle 5k

Sep 20, 2026

straighten

Distance — 5K

terrain

Type — Running

timer

09:00

sell

$30.00

Weather Overview

These values represent the 3-year monthly averages for September in Sleepy Hollow.

Temp (°C)

Feels Like (°C)

thermostat 15.1° / 24.9°

wb_sunny 14.0° / 23.7°

Wind (km/h)

Humidity (%)

air 10.1 /

water_drop 69.7%

Temp (°C)

Feels Like (°C)

Wind (km/h)

Humidity (%)

thermostat 15.1° / 24.9°

wb_sunny 14.0° / 23.7°

air 10.1 km/h

water_drop 69.7%

About Sleepy Hollow

Learn more about the host city, Sleepy Hollow.

Sleepy Hollow is a village in Westchester County in the state of New York. It was one of the settings for Washington Irving's short story "The Legend of Sleepy Hollow".