Welcome to Chestertown
A colonial port town on the Chester River, with brick sidewalks, a working waterfront and a downtown full of galleries, shops and places to eat.
Looking for town government or resident services? Visit chestertown.gov.
Where history meets modern charm
Chestertown was founded in 1706 as a port on the Chester River, and it quickly became one of the busiest trading towns on the Eastern Shore. Ships left the waterfront loaded with tobacco and grain bound for Europe and the Caribbean, and many of those ships were built right here.
The town has its own place in revolutionary history, too. In 1774, residents staged the Chestertown Tea Party, protesting British taxes by throwing tea into the river. In 1782, Washington College was founded with the support of George Washington, who donated 50 guineas and served on its board. It's the oldest college in Maryland and the tenth oldest in the country.
Much of that history is still standing. The historic district is full of beautifully preserved 18th-century homes and storefronts, and today they're filled with galleries, boutiques and restaurants, along with the neighbors who make this such a welcoming place to visit and to live.
A bird's-eye view of Chestertown and its waterfront.
An early street map of the town along the Chester River.
Public Square
A downtown landmark
Paving the way
View of Main Street
Chestertown through the years
Three centuries of milestones, from the colonial charter to the town marina. For a deeper look, the Historical Society of Kent County keeps the town's records, photographs and stories.
- 1706
Chestertown is officially established by colonial charter.
- 1774
Residents stage the Chestertown Tea Party.
- 1782
Washington College is founded under the patronage of George Washington.
- 1890
The Chestertown Electric Company brings electricity to town.
- 1899
The Hebe Fountain is installed in Fountain Park.
- 1970
The Chestertown Historic District is established.
- 1991
The RiverArts organization is founded.
- 2001
The Schooner Sultana is launched.
- 2011
Chestertown hosts its first Downrigging Weekend.
- 2013
The first annual Legacy Day celebration.
- 2016
Chestertown opens a town marina and the Cerino Center.
- 2018
The Chestertown Spy launches.
Come see it for yourself
We'll point you to the best cream of crab soup in town, the ice cream worth the line and the galleries you won't want to miss. Start at the Visitor Center and we'll help you plan the rest of the day.
The Chestertown Chat
Our blog shares stories from visitors and residents who have fallen for this town, along with the hidden spots, local history and small details that make Chestertown feel like home.
