Chestertown
Triathlon Calendar near Chestertown 2026-2027
Monthly updates for Chestertown
Get new running races (and updates) in your inbox every month.
Explore the top triathlons near Chestertown for 2026-2027! We've gathered 6 exciting races in the area. Check out our detailed list below to find your next local race.
October 2026
A two day triathlon festival in Rock Hall, Maryland featuring half, Olympic and sprint distances with triathlon, aquabike and relay options. Swim in Rock Hall Harbor and ride and run on largely flat to rolling rural roads.
A two day triathlon festival at the Hammerman Area of Gunpowder State Park in Chase, MD. It features women's and men's sprint triathlons, aquabike and duathlon options, team relays and a youth race for ages 6 to 15.
Sprint multisport events at Matapeake Beach in Stevensville, MD on October 17, 2026, including triathlon, duathlon, aquabike and relay formats with a 0.5 mile swim, a 12 mile bike out and back on Route 8, and a 3.1 mile run.
June 2027
Olympic and Sprint triathlons in Rock Hall Maryland with protected bay swims, mostly flat bike and run courses, aquabike and relay options over a festival weekend.
July 2027
Experience a premier multisport event in Perryville featuring scenic swims in the Chesapeake Bay and cycling through the rolling farm country of Maryland.
Monthly updates for Chestertown
Get new running races (and updates) in your inbox every month.
August 2027
Triathlon and aquabike races in North East Maryland feature Chesapeake Bay swims, rural hilly bike routes through Elk Neck State Forest, and rolling out and back runs.