Headless Horseman Hussle

SEP

20

2026

Run or walk through the scenic neighborhood streets of Sleepy Hollow at this community event supporting local education. This fundraiser features a 5k course and a 1k option for younger participants.

Sun 20 Sep 2026

Sleepy Hollow, Illinois

Registration

5 kilometers

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Headless Horseman Hussle

The Headless Horseman Hussle is a community running event held in the Village of Sleepy Hollow, Illinois. Participants navigate a course that passes through scenic neighborhood streets starting from Glen Oak Drive. This event serves as a fundraiser for the Sleepy Hollow Elementary PTC, with proceeds benefiting local students, teachers, and school programs.

The following distances are available:

5 km run or walk
1 km walk for younger participants

The event is open to individuals of all ages and abilities. The route is designed to highlight the local residential landscape while providing an outdoor activity for community members. Registration for the event includes a fee, which contributes directly to the Parent Teacher Council's efforts to support educational initiatives and school-based programs. Participants are encouraged to utilize the course for running or walking in a group environment centered on supporting the local elementary school. Visit the organization's website for the most recent information.

5 km

Headless Horseman Hussle 5k

1k Walk