Welcome to Kent County A scenic peninsula, on Maryland’s Upper Eastern Shore of the Chesapeake Bay, the County of Kent is less than a two-hour drive from Philadelphia, Washington D.C., Annapolis and Northern Virginia. Quaint waterfront towns, including Historic Chestertown, Rock Hall, Galena, Betterton and Millington, offer sunset cruise charters, small beaches, kayaking, fishing charters, boating, sailing, museums, theaters, art galleries, brick sidewalk shopping, antiquing, farmers’ and Artisans market, local seafood, including the Chesapeake Bay Blue Crab, Maryland’s second largest collection of 18th century structures and more. In Kent County, Maryland, the War of 1812 was up close and personal. Given the amount of Chesapeake Bay shoreline in the county, British ships and Royal Marines were never very far away. The rivers and creeks exposed even more residents to raids by the enemy. Two of the larger events were the raid on Georgetown and the battle of Caulk's field. There are other locations in Kent County which help tell the story of the War of 1812 on the Eastern Shore. The rural, unspoiled nature of Kent County make it easy to imagine what it must have been like 200 years ago.