Chestertown Challenge Half Marathon Run and 5K Run/Walk

Lace up for the Chestertown Challenge Half Marathon Run and 5K Run/Walk on Sunday, October 11, 2026, in the charming, historic town of Chestertown, Maryland. This event offers both a scenic 13.1-mile half marathon and a 3.1-mile 5K run/walk, starting and finishing at Wilmer Park, nestled alongside the picturesque Chester River. The USA Track & Field-sanctioned course guides runners along entirely paved country roads, featuring gentle rolling terrain and pleasant views of the surrounding countryside and Chestertown's colonial architecture, including its quaint High Street.

Runners can anticipate well-supported courses with water stops strategically placed approximately every two miles on the Half Marathon route, at the 5K turnaround, and at the start/finish area. Restrooms will also be available at the start/finish and along the Half Marathon course for convenience. Typical race day conditions in mid-October offer comfortable temperatures, with highs around 72°F and lows around 57°F, alongside a minimal 13% chance of precipitation, creating an ideal atmosphere for a personal best or an enjoyable cruise.

Beyond the challenge, this race is celebrated for its community spirit and a strong reputation for production and scenery. It proudly benefits the Kent Association of Riding Therapy, Inc. (KART), an organization dedicated to enhancing the social and developmental growth of individuals with disabilities through therapeutic horseback riding. Participants can look forward to quality tech shirts, refreshing food and refreshments at the finish line, and unique awards for top finishers across various categories. Many runners praise the "enjoyable out and back" course, the beautiful river views, and the friendly atmosphere, often returning year after year.