Letter to the Editor: Is Chestertown Maryland’s quintessential New England town?

By Tom Merritt

Guest Contributor

A quaint town in the Mid-Atlantic region, Chestertown has gained significant recognition for its charm and allure. Chestertown is as close to a quintessential New England small town as one can get in Maryland.

“It’s definitely the closest thing I have seen to a typical New England-y town down here,” freshman Ben Dickinson, who hails from Middletown, R.I., said.

There are many similarities between our own Chestertown, Md. and the stereotypical small New England town.

Revolutionary history

Chestertown is rich in American Revolutionary history, as are many New England towns. There was even a “Chestertown Tea Party” which took place in May 1774, a few months after the Boston Tea Party, in which tradition claims that protestors marched to the waterfront and dumped the tea that had arrived from London into the river. Additionally, George Washington visited Chestertown on eight occasions. Thomas Jefferson and Patrick Henry visited the town as well.

Small, private liberal arts college

Chestertown boasts its own private liberal arts college, Washington College. A few New England towns are home to similar schools, namely Amherst College in Amherst, Mass., Williams College in Williamstown, Mass., and Middlebury College in Middlebury, Vt.

Town square

Many towns in New England have a town square in the middle of the downtown area. Chestertown’s downtown is home to Fountain Park and Monument Park.


Chestertown features a plethora of eighteenth-century houses that were once owned by wealthy merchants. Several of these buildings were constructed according to the Federal Style, which was also popular in New England.

Small churches

The steeples of Chestertown’s many churches rise above the smaller buildings in the downtown area.


The Chesapeake Bay region is connected by waterways. Chestertown itself boasts picturesque views of docks, boats, and bridges that call to mind Chatham, Mass. and other towns on the Atlantic seaboard.


An emphasis on agriculture is found in Chestertown and in the surrounding areas. Historically, the Chester River was part of a trade route for much of the Eastern Shore’s produce. The local farmers’ market takes place on Saturday mornings.

Small “mom and pop” shops

A considerable amount of small boutique and artisan businesses dot the downtown corridor along High and Cross Streets.

Overall aura

According to the New York Times, Chestertown offers a “mix of intellectual stimulation and quirkiness.” In this regard, Chestertown rivals the New England towns of Burlington, Vt. or Provincetown, Mass.

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