In 42 days · Sun, Oct 25, 2026
Don't let race day sneak up
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When
Sunday, October 25th, 2026
Where
121 N Bentz St., Frederick MD
Distances
5K
Typical weather
46–64°F · low rain risk
See last 10 years
On this date: rain 2 of the last 10 years
2025
36–58°F
dry
2024
38–64°F
dry
2023
43–73°F
dry
2022
57–67°F
dry
2021
58–77°F
rain
2020
44–52°F
rain
2019
45–64°F
dry
2018
35–53°F
dry
2017
48–61°F
dry
2016
43–57°F
dry
Best months to race in Maryland →
About this race
Event Overview
- Event Name: Headless Horseman Fun Run and 5K
- Date: October 25, 2026
- Location: 121 N Bentz St., Frederick, MD
- Registration Link: Register Here
Description
- Who: The West Frederick MS and Frederick HS PTSAs
- What: A family-friendly event for all ages
- Support: A Steeple Chasers supported race with chipped bibs
- Fun: Costumes are encouraged, and there will be costume contests
Costume Contest Categories
- Best overall
- Scariest
- Funniest
- Most creative
- Best Headless Horseman/Sleepy Hollow
- Best Family/Group
- Best Kids Costume
Community Involvement
- Shoe Collection: We will be collecting shoes for the Stride Forward Youth Program
- Mission: Support underserved cross country and track & field programs
- Action: Please bring your old shoes for a good cause!!
- Program: A student-run nonprofit program in Urbana
Packet Pickup
- Date: Saturday, 10/24 from 1-3 PM
- Location: In front of the Frederick HS
- Race Day Pickup: Available starting at 7:30 AM
Race Details
- 5K Course: Winds through boooo-tiful Baker Park and surrounding neighborhoods
- Fun Run: Starts and finishes at the bandshell in Baker Park
- Area: Stays within Baker Park between Bentz St and College Ave
- Benefit: Proceeds support West Frederick Middle and Frederick High School communities
Proceeds Usage
- Distribution: Proceeds will be divided equally
- Purpose: To support student activities
- Teacher Grants: Funds will assist in granting teacher requests
Course map
Hotels for race weekend
Live prices near the start line, Oct 24 – 26, 2026.
Train with a club
Run clubs near Frederick to train with before race day.
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