HEADLESS HORSEMAN FUN RUN & 5K 2026 — Frederick, MD

Date
October 25, 2026
Location
Frederick, MD
Venue
21 N Bentz St.
Start Time
8:30 AM
Entry Fee
$20.00 – $35.00
Events
1K Fun Run, Headless Horseman 5K (Ages 12 & Under), Headless Horseman 5K (Ages 13 -64), Headless Horseman 5K (Ages 65 & Up)
Includes
T-Shirt
Register NowRegistration Open
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! 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.

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HEADLESS HORSEMAN FUN RUN & 5K 2026 — Frederick, MD

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Race Travel Insurance

Don't forget travel insurance for October 25.

You've trained for months and booked a trip to Frederick, MD. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.

  • Trip cancellation up to 100% of prepaid costs
  • Running events covered under standard plans — no add-ons needed
  • Trip interruption up to 150% of non-refundable costs
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support
Get a Quote — Faye Travel Insurance

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Frequently Asked Questions

When is HEADLESS HORSEMAN FUN RUN & 5K 2026 — Frederick, MD?

HEADLESS HORSEMAN FUN RUN & 5K 2026 — Frederick, MD takes place on October 25, 2026. The race is held in Frederick, Maryland.

Where is HEADLESS HORSEMAN FUN RUN & 5K 2026 — Frederick, MD held?

HEADLESS HORSEMAN FUN RUN & 5K 2026 — Frederick, MD is held at 21 N Bentz St. in Frederick, Maryland.

Where can I find hotels near HEADLESS HORSEMAN FUN RUN & 5K 2026 — Frederick, MD?

RaceHotelFinder shows hotels sorted by distance from the race venue in Frederick. Use the map or list view on this page to compare options and book race weekend accommodation.