Chestertown Challenge Half Marathon

OCT
11
2026
The Chestertown Challenge offers a half marathon and 5K around Wilmer Park in Chestertown, Maryland, with proceeds benefiting the Kent Association of Riding Therapy. Courses run on paved country roads with water stations, marked miles, and finish-line refreshments.
Sun 11 Oct 2026
13 miles 5 kilometers

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Chestertown Challenge Half Marathon Run and 5K Run/Walk

The Chestertown Challenge includes a half marathon plus 5K run and 5K walk events, and a Silent Hero registration option for supporters who cannot attend. The event takes place at Wilmer Park in Chestertown, Maryland, with the start and finish located at the park. Wilmer Park is described as being across the street from 400 South Cross Street.

The course is run entirely on paved country roads and features gentle rolling terrain. Water stops are provided roughly every two miles on the half marathon, at the 5K turnaround, and at the start/finish. Restrooms are available at the start/finish and on the half marathon course. The course is marked with mile markers and directional arrows, and roads are police controlled.

Awards are given to overall male and female winners in the half marathon and 5K run, with top two finishers in 10-year age groups also recognized for those races. The 5K walk awards go to the top two male and female finishers. Race packets can be picked up on race morning, and race day registration is available. Tech shirts are guaranteed to participants registered by September 30th. Food and refreshments are provided at the finish line.

The event benefits the Kent Association of Riding Therapy, which offers therapeutic horseback riding, barn management, and related programs to people with disabilities. Visit the organization's website for the most recent information.

13 mi
Half Marathon
5 km
5k Run
5 km
5k Walk