HEADLESS HORSEMAN FUN RUN & 5K logo

HEADLESS HORSEMAN FUN RUN & 5K

HEADLESS HORSEMAN FUN RUN & 5K is a running race on October 24, 2027 in Frederick, MD, with entry fees from $20 to $35.

Date
October 24, 2027 (346 days to go)
Price
$20–$35
Sport
Running

From the Organizer

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.

Events

1K Fun Run$20
Headless Horseman 5K (Ages 12 & Under)$30
Headless Horseman 5K (Ages 65 & Up)$30
Headless Horseman 5K (Ages 13 -64)$35

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.

Sunrise 7:28 AMSunset 6:18 PMDaylight 10h 50m

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

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.

346

Days to train

Race
HEADLESS HORSEMAN FUN RUN & 5K
Date
October 24, 2027

Get Ready for Race Day

Plan your training, log every workout, and track your progress all the way to race day in the Endurance Grid app.

The training calendar in the Endurance Grid app: the week plan and every day colored by sport
A Race Story in the Endurance Grid app: the finish photo and everyone who finished

Frequently Asked Questions

What is the HEADLESS HORSEMAN FUN RUN & 5K?
HEADLESS HORSEMAN FUN RUN & 5K is a running race held in Frederick, Maryland on October 24, 2027. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more running races near you or explore our sports guides to learn what race day actually feels like.
When and where is the HEADLESS HORSEMAN FUN RUN & 5K?
Sunday, October 24, 2027 in Frederick, Maryland at 121 N Bentz St.. Check the event page for exact start times and wave schedules.
How do I register for the HEADLESS HORSEMAN FUN RUN & 5K?
Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.

HEADLESS HORSEMAN FUN RUN & 5K

Oct 24, 2027

Register