Chestertown Challenge Half Marathon Run and 5K Run/Walk
Sun, Oct 11, 2026, 5:00 AM EDT
- Type
- Run
Finish signup on the organizer site (check fees and dates there).
Race feel
Run the Chestertown Challenge Half Marathon or 5K on paved country roads, supporting therapeutic horseback riding for those with disabilities.
- Competitive
- For a Cause
Competitive
For a CauseGreat for
- Beginner Friendly
- Military & First Responders
Beginner Friendly
Military & First RespondersJoin the Chestertown Challenge Half Marathon or 5K Run/Walk in Chestertown, MD, offering a chance to run on paved country roads with gentle rolling terrain. This event proudly supports the Kent Association of Riding Therapy (KART), an organization dedicated to enhancing the social and developmental growth of children and adults with disabilities through therapeutic horseback riding. Participants can look forward to quality tech shirts, finish line refreshments, and unique awards for top finishers across various categories.
What to expect
- Enjoy a course entirely on paved country roads with gentle rolling terrain.
- Water stops are available approximately every two miles on the Half Marathon course.
- Receive a quality tech shirt and enjoy refreshments at the finish line.
Standout details
- Benefits Kent Association of Riding Therapy
- Paved country roads, gentle rolling terrain
- Unique awards for overall and age group winners
- Quality tech shirts for participants
Perks & features
- Awards
AwardsFrom the public listing; confirm on the official site.
Distances & registration
4 optionsUse the official signup link above for all distances.
5K
2 options · closes Oct 11, 2026, 5:00 AM EDT
5mo 11d 19h 51m leftRun
Closes Oct 11, 2026, 5:00 AM EDT · From $28.00
WALK
Closes Oct 11, 2026, 5:00 AM EDT · From $28.00
Half Marathon
1 option · closes Oct 11, 2026, 5:00 AM EDT
5mo 11d 19h 51m leftGeneral entry
Closes Oct 11, 2026, 5:00 AM EDT · From $54.50
Other options
1 option · closes Oct 11, 2026, 5:00 AM EDT
5mo 11d 19h 51m leftSilent Hero
Closes Oct 11, 2026, 5:00 AM EDT · From $33.30
Summaries use public event text. Confirm schedule, fees, and rules on the official page before you sign up.
From the organizer
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