Chestertown Challenge Half Marathon

Lace-up for an unforgettable autumn run at the Chestertown Challenge Half Marathon on October 11, 2026, in the historic town of Chestertown, Maryland. Offering both a scenic 13.1-mile half marathon and a spirited 5K, this event promises a rewarding experience for runners of all levels. Starting and finishing in beautiful Wilmer Park, nestled alongside the Chester River, the out-and-back course treats participants to a charming blend of historic colonial architecture as they pass through town, before venturing onto gently rolling, paved country roads with picturesque views of the surrounding green hills and countryside.

Runners can anticipate well-supported race day conditions, with historical weather for this time of year typically featuring comfortable highs around 72°F and lows around 57°F, alongside a modest 13% chance of precipitation. Aid stations are strategically placed approximately every two miles along the half marathon route, at the 5K turnaround, and at the start/finish line, ensuring hydration and support. Restrooms are also available at the start/finish area and on the half marathon course. Beyond the personal challenge, the Chestertown Challenge holds a special significance, benefiting the Kent Association of Riding Therapy, Inc. (KART), which utilizes therapeutic horseback riding to enhance the social and developmental growth of individuals with disabilities. Participants can look forward to quality tech shirts for early registrants, unique awards for top finishers, and invigorating post-race refreshments, all contributing to a memorable day on police-controlled roads with clear mile markers and directional arrows.