Chestertown Challenge Half Marathon Run and 5K Run/Walk
- Date Sun 11th October 2026
- Time 9:00AM EDT
- Location Chestertown, Maryland
- Price $28.00 - $54.50
- Races 4 races
- Distances Half Marathon, 5km
Event summary
Join the excitement at the Chestertown Challenge Half Marathon Run and 5K Run/Walk on Sunday, October 11, 2026, in the picturesque town of Chestertown, Kent. This vibrant event, starting at Wilmer Park at 9 a.m., features two thrilling race distances: a challenging Half Marathon and a fun-filled 5K Run/Walk, making it perfect for runners of all levels. Registration opens at 8 a.m., with race day registration available for those who want to join in the fun last minute!
The Chestertown Challenge is not just about the race; it also supports a great cause, benefiting the Kent Association of Riding Therapy, Inc. (KART), which provides therapeutic horseback riding for individuals with disabilities. Participants can look forward to unique awards for winners in both races, quality tech shirts for early registrants, and delicious food available for purchase at the finish line. With scenic views along the Chester River and a supportive atmosphere, this event promises to be a highlight of the fall season. Don’t miss out on a day filled with community spirit, fitness, and fun!
The Chestertown Challenge is not just about the race; it also supports a great cause, benefiting the Kent Association of Riding Therapy, Inc. (KART), which provides therapeutic horseback riding for individuals with disabilities. Participants can look forward to unique awards for winners in both races, quality tech shirts for early registrants, and delicious food available for purchase at the finish line. With scenic views along the Chester River and a supportive atmosphere, this event promises to be a highlight of the fall season. Don’t miss out on a day filled with community spirit, fitness, and fun!
Organiser's Description
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!
Food for Purchase will be available!
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 - 127 - 2014, Female Meredith Tulio - 129 - 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 [https://www.kentcounty.com/lodging/rockhall_lodging.php]
Inns & Bed and Breakfast in Chestertown, Maryland [https://www.kentcounty.com/lodging-type/inns/chestertown]
Red Roof Inn & Suites Chestertown - ReservationDesk.com [https://www.reservationdesk.com/hotel/69216f9/red-roof-inn--suites-chestertown-chestertown-maryland/]
Comfort Inn & Suites Chestertown - ReservationDesk.com [https://www.reservationdesk.com/hotel/6125f0d/comfort-inn--suites-chestertown-maryland/tertown]
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!
Food for Purchase will be available!
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 - 127 - 2014, Female Meredith Tulio - 129 - 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 [https://www.kentcounty.com/lodging/rockhall_lodging.php]
Inns & Bed and Breakfast in Chestertown, Maryland [https://www.kentcounty.com/lodging-type/inns/chestertown]
Red Roof Inn & Suites Chestertown - ReservationDesk.com [https://www.reservationdesk.com/hotel/69216f9/red-roof-inn--suites-chestertown-chestertown-maryland/]
Comfort Inn & Suites Chestertown - ReservationDesk.com [https://www.reservationdesk.com/hotel/6125f0d/comfort-inn--suites-chestertown-maryland/tertown]
Races
-
Half Marathon
Incl. $4.50 Fee & T-Shirt
Sun 11th October 2026 (9:00AM EDT)
$54.50
-
5K Run
Incl. $3.00 Fee & T-Shirt
Sun 11th October 2026 (9:00AM EDT)
$28.00
-
5k Walk
Incl. $3.00 Fee & T-Shirt
Sun 11th October 2026 (9:00AM EDT)
$28.00
-
Silent Hero
Incl. $3.30 Fee
Sun 11th October 2026 (9:00AM EDT)
$33.30
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Wilmer Park, Chestertown, 21620, MD, United States
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Chestertown Challenge Half Marathon Run and 5K Run/Walk
