Waterfront of Chestertown

Chestertown in the County of Kent

Beautifully preserved National Register river town on Maryland's Eastern Shore whose architecture spans 300 years …

Chestertown, an Eastern Shore tidewater community founded in 1706, lies the county seat of Kent County, Maryland. Located in the arable countryside north of the Chesapeake Bay Bridge with a southern boundary formed by the placid Chester River, Chestertown is home to 4,500 residents. 

In the 18th century, Chestertown was an important port in the colonial trade with London, until local patriots threw a cargo of dutiable tea overboard in 1774. Every year, locals celebrate the rebelliousness of their forebears with an annual Tea Party celebration.

Today, Chestertown is a vibrant community with a solid foundation in its historic roots. Chestertonians and visitors alike enjoy the sense of tradition and timelessness that the town emanates. Washington College, the liberal arts institution graced with its moniker by George Washington himself, contributes much to the intellectual sophistication of the town, as it has for almost 250 years from its situation on the highest point in the natural terrain.Osprey perched on it's nest along the Chester River

Within a few blocks from the waterfront docks, one can tour a 18th century customs house, sail on a reproduction schooner from the 1700’s, drink a drug-store fountain soda mixed to your pleasure, and take in a thoroughly modern rock ensemble. Neighbors and strangers greet each other casually on Chestertown’s brick-paved sidewalks. A deep, and obvious, Sense of Place pervades.

Chestertown is a swift 50-minute drive from Annapolis, 1.5 hours from Baltimore, Washington and Philadelphia. New York lies 3.5 hours away.

Thank you …

The Finishing Touch for the use of the Chester River Riverscape photo and to Mullin/Ashley Associates for website design and development

The Latest

Sensing Change
Programs Exploring
Interaction of 
Science & Art
Various Venues

Inaugural Cruise
Sunday Brunch
Chester River

Sunday April 6
  11:30 am

Kent County
 Poetry Festival

Friday April 11

Shoot For the Stars!

Casino Night
Saturday April 12

Garfield Center
7 pm

Health Aging 

Tuesday April 15
 Middle School
8 am - 1 pm
Earth Day Festival
& Mutt Strut
Saturday April 19
Memorial Row
 9 am - 1 pm

War of 1812

Cruise & Lecture
Friday April 25
River Packet
5;30 -?


Paint the Town

Wet Paint Show
Saturday April 26
RiverArts Gallery
5 - 8 pm


Taste of the Town

Sunday April 27
Fountain Park
noon - 3 pm

Wednesday April 30
5:30 pm

Open Mic Night
Wednesday April 30
Garfield Center






more info on DCA


Interactive Digital Sign




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