The Chester River is a major tributary of the Chesapeake Bay on the Delmarva Peninsula.

Chestertown, the seat of Maryland's Kent County, is located on its north shore.

It ends at the Chesapeake Bay in a very wide mouth between Love Point on Kent Island, and Swan Point, near Gratitude, Maryland.

Local lore has it that in 1774, colonists boarded a British ship anchored in the Chester River at Chester Town, also called New Town on Chester, and threw its load of tea overboard, mimicking the Boston Tea Party and its act of defiance against King George III.

While primary source documents show that Chestertown residents did have at least one meeting to discuss the presence of tea aboard the locally owned merchantman Geddes, and later the residents sent food to aid the blockaded Bostonians, contemporaneous source material has yet to be found.