Welcome to Chestertown

Founded in 1706

Chestertown was founded in 1706, officially established by colonial charter as part of Queen Anne’s County, Maryland. It was originally known as “New Town” or “Newtown” and was intended to serve as a port and trading center along the Chester River, which flows into the Chesapeake Bay. The town’s location made it an ideal hub for trade and commerce in the region.

By the mid-18th century, Chestertown had become a bustling port town, exporting tobacco, grain, and other goods to Europe and the Caribbean. It also became a center for shipbuilding, with many vessels constructed along its waterfront.

During the American Revolution, Chestertown was a hotbed of revolutionary activity. In 1774, the residents of Chestertown staged the Chestertown Tea Party, in which they protested British taxation by throwing tea into the Chester River, in imitation of the Boston Tea Party.

Chestertown is home to Washington College, which was founded in 1782 and is the 10th oldest college in the United States and the oldest college in Maryland. It was founded under the patronage of George Washington, who donated 50 guineas to the college and served on its Board of Visitors and Governors.

After the Revolution, Chestertown continued to thrive as a center of trade and commerce. In the 19th century, it became known for its manufacturing industries, including textiles, shoes, and canned goods. The town’s economy also benefited from its location on the Eastern Shore of Maryland, which made it a transportation hub for goods moving between Baltimore, Philadelphia, and other cities.

Today, Chestertown is known for its historic architecture, charming streets, and vibrant arts scene. It remains an important cultural and economic center on Maryland’s Eastern Shore.