Headless Horseman Fun Run & 5K - Frederick

OCT

25

2026

Family friendly 1K fun run and 5K in Baker Park with costume contests, candy, and chipped bibs; event proceeds support local school PTSA programs.

Sun 25 Oct 2026

Frederick, Maryland

Website

5 kilometers

Always double-check with the organizer's website! This page may contain affiliate links.

HEADLESS HORSEMAN FUN RUN & 5K : Frederick, MD

The Headless Horseman Fun Run and 5K is a family friendly run held in Frederick that benefits West Frederick Middle and Frederick High School communities. Proceeds are divided equally between the two PTSAs and will support student activities or teacher grants.

The event includes both a shorter fun run and a 5K. The 5K course winds through Baker Park and surrounding neighborhoods. The fun run starts and finishes at the bandshell and stays within Baker Park between Bentz Street and College Avenue. The race is supported by Steeple Chasers and uses chipped bibs for timed results.

Costumes are encouraged and there will be multiple costume contests with categories such as Best Overall, Scariest, Funniest, Most Creative, Best Headless Horseman / Sleepy Hollow, Best Family or Group, and Best Kids Costume. Candy will be available during the event.

Distances: Visit the organization's website for the most recent information.