Chestertown Challenge Half Marathon & 5K

Sunday, October 13, 2024 • Chestertown, MD • Course Map

runsignup-blueA benefit for a pair of locally based nonprofits working to preserve the Chester River and the natural treasures of Maryland’s Chesapeake Bay, this race takes runners on an out-and-back route along the rolling rural roads just outside this town.

The race takes runners through charming Chestertown, founded in 1806 and today home to just over 5,200 residents, where the historic colonial architecture of its heyday as a port and shipping center are still preserved, especially along its quaint main thoroughfare, High Street.

Runners will get to see much of the countryside just outside the town during the race, with plenty of rolling green hills along the way. They’ll follow an out-and-back course for the race, which starts and finishes in Wilmer Park, nestled right along the banks of the Chester River, just across the river from Kingstown.

From there, they’ll head out on a USA Track & Field-sanctioned 13.1-mile route through town and the outskirts of town, along terrain organizers say is “gently rolling” and with plenty of views of the countryside.

Water stations will be provided at about every 2 miles along the half marathon route, organizers note, as well as at the start and finish line area and the turnaround point of the 5K course.

The race is organized by the Maryland-based TriSports Events, and is part of its Team TriSports Events Ultimate Challenge Series — the race benefits both the Chester River Association, which works to preserve the ecosystem around the river, and Sultana Projects, which works to preserve the history of Chesapeake Bay.

Race Weather & Climate

Located near the head of the Chester River here in eastern Maryland, across the Chesapeake Bay from Baltimore and Annapolis, Chestertown typically sees October temperatures that average between the high 40s and the low 70s, while rainfall totals average just over 3.3 inches for the month.

Day of Race

  • Avg. Low: 52°F
  • Avg. High: 72°F

Course Map

See the race route map for the Chester River Challenge Half Marathon.

Starting Time

9:00 AM


  • $50 – $60 for the half marathon
  • $25 – $30 for the 5K


To reserve your spot in the 2024 running of Chestertown’s Chester River Challenge Half Marathon or 5K race, register online at


Official Race Website


Ever run in the Chester River Challenge? Share your impressions here, or post your review in the Comments below.

See more races in: October, Maryland