The Chester River is one of the largest rivers on the eastern side of the Chesapeake Bay Watershed.
The Chester River begins near Millington, Maryland, at the convergence of Cypress Branch and Andover Branch. Along its length the river is joined by Langford Creek, Morgan Creek, the Corsica River, Southeast Creek, and numerous small tributaries. The river converges with the Chesapeake Bay near Love Point.
The main entrance to Chester River is between Love Point at the northern end of Kent Island, and Eastern Neck Island. The approach is northward and eastward of Love Point Light. The river is navigable up to Crumpton MD.
Since colonial times, the Chester has been known for its oyster production. Home to numerous natural oyster bars and reefs, production declined over time as water quality and other factors took their toll.
Many areas of the Chester River bottom are currently designated as oyster sanctuaries. In 2021, the EPA approved the Chester River and its tributaries as a No Discharge Zone (NDZ).
Each fall, the annual Downrigging Festival Weekend is held in Chestertown along the waterfront.
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