HEADLESS HORSEMAN FUN RUN & 5K
HEADLESS HORSEMAN FUN RUN & 5K is a running race on October 25, 2026 in Frederick, MD, with entry fees from $20 to $35.
- Date
- October 25, 2026 (43 days to go)
- Location
- 121 N Bentz St., Frederick, MD
- Price
- $20–$35
- Sport
- Running
From the Organizer
The West Frederick MS and Frederick HS PTSAs are bringing back the Headless Horseman Fun Run and 5K! This is a very family friendly event for all ages, as well as a Steeple Chasers supported race with chipped bibs to encourage our competitive runners to be scary fast! Costumes are encouraged, and there will be costume contests. And candy...lots of candy!!
Costume Categories include:
Best overall
Scariest
Funniest
Most creative
Best Headless Horseman/Sleepy Hollow
Best Family/Group
Best Kids Costume
We will also be collecting shoes for the Stride Forward Youth Program, a student run nonprofit program in Urbana with a mission to support underserved cross country and track & field programs by collecting and donating gently used running shoes to student athletes who need them. PLEASE BRING YOUR OLD SHOES FOR A GOOD CAUSE!!
Packet Pickups will occur on Sat, 10/24 from 1-3 in front of the Frederick HS. You can also pick up the day of the race, starting at 730a.
The 5K course will wind its way through boooo-tiful Baker Park and the surrounding neighborhoods; the Fun Run will start and finish at the bandshell, staying within Baker Park between Bentz St and College Ave.
This fun event will benefit both the West Frederick Middle and Frederick High School communities. Proceeds will be divided equally and will be used to support student activities or teacher grants.
Events
Weather
Typical Conditions
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
65°
Typical Low
44°
Chance of Rain
21%
Based on US Climate Normals data from Frederick Police Brks, 1 mi from the venue.
Host City
About Frederick, MD
Population
80,617
as of 2023
City Elevation
329 ft
Nearest Airport
HGR
Hagerstown Regional Richard A Henson Field · 26 mi
Major Hub
IAD
Washington Dulles International Airport · 33 mi
Time Zone
Eastern Time
From Endurance Grid
A mid-size host city. Enough lodging and amenities to keep race weekend easy, without big-city sprawl.
Race Location
Your Next Start Line
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at HEADLESS HORSEMAN FUN RUN & 5K, put it on the calendar, and turn “someday” into a start date.
43
Days to train
- Race
- HEADLESS HORSEMAN FUN RUN & 5K
- Date
- October 25, 2026
- Location
- 121 N Bentz St., Frederick, MD
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From Endurance Grid
About This Sport
Endurance Grid is here to help you understand the sport, decide if it’s the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.
With running, there's a distance for every fitness level, a community at every start line, and nothing beats the feeling of crossing a finish line you trained for.
Running is an endurance sport that rewards consistency, and showing up every week compounds in ways that will surprise you.
Running
From 5K to marathon, running races are an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Coming Up
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Frequently Asked Questions
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HEADLESS HORSEMAN FUN RUN & 5K
Oct 25, 2026