Chestertown Challenge Half Marathon Run and 5K Run/Walk

Sun, Oct 11, 2026 Β· πŸ“ Chestertown, MD
DateπŸ“… Sun, Oct 11, 2026
LocationπŸ“ Chestertown, MD
View on map β†’ Register for This Race β†’

Get ready to run for a great cause in Chestertown! Whether you're tackling the half marathon or enjoying the 5K run/walk, you'll be supporting the Kent Association of Riding Therapy, Inc. (KART), an organization that's been helping children and adults with disabilities build confidence and skills since 1984 through therapeutic horseback riding and equine care programs. Head to Wilmer Park on race morning starting at 8 a.m. for packet pickup and registration, with both events kicking off at 9 a.m.β€”and don't worry, you can even register the day of the race!

Not Sure You're Ready?

Take our free 3-question quiz and get matched to a training plan built for your fitness level.

Get My Training Plan β†’
Sun, Oct 11, 2026
Chestertown Challenge Half Marathon Run and 5K Run/Walk
Register β†’

Running a 5K?

Take our 5K Training Quiz to find the RIGHT training plan for you.