Chestertown Challenge Half Marathon
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Chestertown Challenge Half Marathon and 5K - Chestertown, MD (October 11, 2026)
The event offers multiple entry options: a Half Marathon, 5K Run, 5K Walk, and a Silent Hero option to support the beneficiary without attending. The race benefits the Kent Association of Riding Therapy (KART), an organization that provides therapeutic horseback riding and related programs for children and adults with disabilities.
Course, logistics and awards
All races start and finish at Wilmer Park in Chestertown. The courses run entirely on paved country roads and feature gentle rolling terrain. Water stops are provided approximately every two miles on the half marathon, at the 5K turnaround, and at the start/finish. Restrooms are available at the start/finish and along the half marathon course. Police-controlled roads, mile markers, and directional arrows are used on the course. Tech shirts are guaranteed to participants who register by Monday, September 30. Food and refreshments are available at the finish line.
Awards include unique overall awards for male and female winners of the half marathon and 5K run, top-two awards in 10-year age groups for those races, and top-two male and female awards in the 5K walk. Course record times are listed for the half marathon and 5K run. Visit the organization's website for the most recent information.
