Chestertown was built on the Chester River, 20 miles northeast of the Chesapeake Bay.

It is in the historic district near the Chester River.

The historic residential area is concentrated along Water Street between the business district and the Chester River.

The river begins near Centreville and empties into the Chester River.

The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy.

Chestertown was incorporated in 1805, and was named for the Chester River.

The highway was extended south from Lambson to the Chester River in 1929 and 1930.

The Chester River would lure more than a hundred thousand and the Miles the same.

The squad continued to practice at St. Andrews and used the Chester River as much as possible.

Millington is the head of navigation for the Chester River.