Chestertown Challenge Half Marathon Run and 5K Run/Walk 2026

The race.

On October 11, 2026, Chestertown, Maryland hosts a half marathon and 5K run/walk at Wilmer Park, benefiting Kent Association of Riding Therapy (KART). Both races start at 9 a.m. on a paved country road course with gentle rolling terrain. Packet pickup and race day registration open at 8 a.m. Overall and age-group awards are presented to top finishers; half marathon awards are given three hours after the start and 5K awards follow the last finisher. Participants registered by September 30th receive a tech shirt, and food and refreshments are available at the finish line. Water stops serve the half marathon course at roughly two-mile intervals and the 5K turnaround, with restrooms at the start/finish and along the half marathon route.