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Headless Horseman Hussle logo

Headless Horseman Hussle

Sun, Sep 20, 2026, 9:00 AM CDT

Location
Sleepy Hollow, IL
898 Glen Oak Dr, 60118
Featured distance
5K
Type
RUN
Official registration

Sign up and verify details on the organizer’s official page.

At a glance

Run or walk a scenic 5K through Sleepy Hollow, supporting local students and school programs with every step.

  • Fun
  • Scenic
  • For a Cause

Great for: cause-driven runners

The Headless Horseman Hussle 5K invites runners and walkers of all ages and abilities to enjoy a community-focused event through the beautiful Village of Sleepy Hollow. This energizing race serves as a fundraiser for the Sleepy Hollow Elementary PTC, with all proceeds directly supporting local students, teachers, and school programs. It's a wonderful opportunity to stay active, enjoy scenic neighborhood streets, and contribute to education in the community.

What to expect

  • A welcoming 5K run/walk for all ages and abilities.
  • Enjoy scenic neighborhood streets in the beautiful Village of Sleepy Hollow.
  • Support local education as proceeds benefit the Sleepy Hollow Elementary PTC.

Standout details

  • Fundraiser for local school programs
  • Scenic neighborhood streets
  • Open to all ages and abilities
  • Optional 1K walk for younger participants

Auto-drafted from the public listing — confirm details on the official event page before signing up.

Vibe Check

Easygoing

  • Rolling area

Based on terrain, weather, and distance data.

The course

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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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