
HEADLESS HORSEMAN FUN RUN & 5K is a running race on October 24, 2027 in Frederick, MD, with entry fees from $20 to $35.
The West Frederick MS and Frederick HS PTSAs invite you to join us for the Headless Horseman Fun Run, 5K, and costume contest! This is a 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!
REGISTER BY 10/08/27 TO ENSURE YOU GET A T-SHIRT. The 2027 shirt will be designed by a WFMS student, so you don't want to miss out!!
The Fun Run will start at 8:30, the costume contest winner will be announced at 8:50 and the 5K will start at 9:15.
Costume Categories include:
Best overall
Scariest
Funniest
Most creative
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, 10/23 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.
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.
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.
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.
346
Days to train
Plan your training, log every workout, and track your progress all the way to race day in the Endurance Grid app.


HEADLESS HORSEMAN FUN RUN & 5K
Oct 24, 2027