Dorchester County is one of the original counties of Maryland, formed before April 13, 1669. The area was home to Nanticoke and Abacos Indians. Settlers from England began to claim lands in the mid 1600's under land grants from Lord Baltimore. Nearly 500 settlers lived in the area by the time of the county's formation. The original boundaries of Dorchester County extended northwest along the Choptank River into New Sweden (Delaware), and all that would become Dorchester County. Today, the county encompasses less than one-half its original size.
The county is named after the Earl of Dorset, a family friend of the Dorchesters. The county seat is Cambridge. This county is the setting for the famous best-selling novel by James A. Michener, Chesapeake .
Dorchester County is called "The Heart of the Eastern Shore" because its mid-shore location and its geographic configuration is heart-shaped. Throughout history, renowned individuals have called Dorchester County home: Patty Cannon, a ruthless slave trader; Harriet Tubman, the "Moses of her people" who helped over 300 slaves find freedom through the Underground Railroad during the Civil War; and Annie Oakley, famed sharpshooter.