Chestertown Challenge Half Marathon Run and 5K Run/Walk
Chestertown Challenge Half Marathon Run and 5K Run/Walk logo

Chestertown Challenge Half Marathon Run and 5K Run/Walk

Chestertown, Maryland, United States View on map
Oct 11, 2026 (America/New_York local time)
Running

About this race

Benefits: Kent Association of Riding Therapy, Inc. (KART)

Registration opens at 8 a.m. - Half Marathon Run & 5K Run/Walk start at 9 a.m.

Registration: Race day registration will be available! Packet pickup starts at 8 a.m. and races start at 9 a.m. at Wilmer Park, Chestertown, Maryland.

Silent Hero Donation: Can't make this event but would like to show your support? Register as a Silent Hero!

Benefactor: Kent Association of Riding Therapy (KART) was founded in 1984 to help children and adults with disabilities enhance their social and developmental growth. KART uses a multi-faceted program involving therapeutic horseback riding, barn management, and caring for the horse.

Packet Pickup: All race packets can be picked up on Sunday morning starting at 8 a.m. Race day registration will also be accepted at this time.

Directions: Wilmer Park is located across the street from address 400 South Cross Street, Chestertown, MD. For directions, use your GPS or MapQuest.

Awards: Unique awards for overall male and female winners in the Half Marathon and 5K Run. Awards presented to the top 2 in 10-year age groups in the Half Marathon and 5K Run. Awards to top 2 male and female finishers in the 5K walk. 5K awards will be presented after the last participant finishes. Half Marathon awards will be presented 3 hours after start.

Course: The event starts and finishes at Wilmer Park. The course has gentle rolling terrain and is run entirely on paved country roads. 

Course Records: Half Marathon: Male - Hasan Butler - 1:21:27 - 2014, Female – Meredith Tulio  - 1:28:29 - 2018. 5K Run: Male - Jesse Goodyear - 17:50 - 2015, Female – Lisa Victorius - 20:50 - 2017

Amenities: Quality “Chestertown Challenge Half Marathon & 5K Run/Walk” Tech Shirts guaranteed to all participants registered by Monday, September 30th. Food and refreshments at the finish line! Police controlled roads, mile markers and directional arrows on road.

Water stops: Water stops will be located at approximately every two miles on the Half Marathon course, at the turnaround of the 5K, and at the start/finish.

Restrooms: Restrooms will be available at the start/finish and on the Half Marathon course.

Spectators: While you're waiting for your friends or family members to complete the race, enjoy the beautiful historic Chestertown sites on the Chester River. Visit www.kentcounty.com/tourism.

Hotels/Motels/Bed & Breakfast: Visit the following websites for a complete list of hotels/motels and bed & breakfast in the Chestertown and Rock Hall area.,
www.kentcounty.com/lodging/rockhall_lodging.php

Inns & Bed and Breakfast in Chestertown, Maryland

Red Roof Inn & Suites Chestertown - ReservationDesk.com

Comfort Inn & Suites Chestertown - ReservationDesk.com

Pick your distance

Running

Half Marathon

Oct 11, 2026 Half-Marathon 9:00 AM
$50.00
Open

5K Run

Oct 11, 2026 5K 9:00 AM
$25.00
Open

Walking

5K WALK

Oct 11, 2026 5K 9:00 AM
$25.00
Open

Typical race-day weather

Based on 10 years of historical conditions on this event's race dates in Chestertown.

Temp (°C)
Minimum temperature (race-day average) 12.7° / Maximum temperature (race-day average) 20.6°
Feels Like (°C)
Minimum feels like — heat index / wind chill (race-day average) 12.7° / Maximum feels like — heat index / wind chill (race-day average) 20.6°
Wind (km/h)
Average wind speed (race-day average)
19.8
Precip (mm)
Average precipitation (race-day average)
5.7mm
Humidity
Average relative humidity (race-day average)
73.8%

Course

Route map and elevation profile

No course map published yet.

The organizer hasn't released a route for this event, and we don't publish guesses. If you're the organizer, send us a GPX file and we'll draw the profile.

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Other races near Chestertown

Different organizers, within 40 miles, in the next three months

Where this page comes from. Race details were last updated on . We re-check listings regularly and again in the week before race day.

  • Entries, prices, waves and inclusions — the event's official registration page
  • Temperature and humidity — Copernicus ERA5 reanalysis via Open-Meteo (CC BY 4.0)
  • Elevation and terrain relief — Copernicus DEM GLO-90, ESA (CC BY 4.0)
  • Comparisons and counts — Race Discovery calendar, 1 Chestertown event

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