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Middlesex County is located at the eastern end of Virginia's Middle Peninsula. The County is bounded by the Rappahannock River to the north, by the Chesapeake Bay to the east, by the Piankatank River and Dragon Run Swamp to the southwest, and by Essex County to the northwest. The County has a land area of 132 square miles (83,392 acres) and 135 linear miles of shoreline.
The County's only town, Urbanna, was established in 1680 serving initially as a port for shipping agricultural products and later as the County's commercial and governmental center.