Chestertown Challenge Half Marathon

OCT
11
2026
Experience the historic charm of Chestertown during a half marathon or 5K run held on paved country roads. Support the Kent Association of Riding Therapy while enjoying a scenic course with rolling terrain and post race refreshments.
Sun 11 Oct 2026
13 miles 3 miles

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Chestertown Challenge

The Chestertown Challenge features long-distance and short-distance events taking place in Maryland. Participants start and finish at Wilmer Park, located near the Chester River in historic Chestertown. The event supports the Kent Association of Riding Therapy (KART), an organization that provides therapeutic horseback riding and barn management programs for children and adults with disabilities.

The available distances include:

  • Half Marathon (13.1 miles)
  • 5K Run (3.1 miles)
  • 5K Walk (3.1 miles)

The course consists of paved country roads with a gentle rolling terrain. For safety and navigation, the roads are police-controlled, and the route is marked with mile markers and directional arrows. Water stations are positioned approximately every two miles for the Half Marathon and at the turnaround point for the 5K. Restrooms are available at the start and finish area, as well as along the Half Marathon course.

Participants who register by the end of September are guaranteed a technical shirt. Following the completion of the races, food and refreshments are provided at the finish line. Awards are presented to the overall top male and female finishers, as well as the top two finishers in ten-year age groups for the running events. The 5K Walk also recognizes the top two male and female finishers. Those who wish to support the cause but cannot attend the physical event may register as a Silent Hero. Visit the organization's website for the most recent information.

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