About Chestertown

Chestertown's history dates back to its founding in 1703. In the mid-eighteenth century, the town became one of Maryland's leading ports, second only to Annapolis. Chestertown's downtown historic district has been preserved in a way that few others can match. Most shops, restaurants, and other enterprises are located in authentic buildings that have been preserved for one, two or three centuries. In fact, even today Chestertown is second only to Annapolis in terms of its number of existing eighteenth century homes.

The Chester River

Chestertown, as well as Heron Point, is built beside the Chester River. At the foot of High Street and following along Water Street is the harbor of Chestertown. Numerous boats are berthed here, and with little effort you can sense Chestertown's role as an important port both before and for a long time following the Revolutionary War.

Heron Point is located about a half mile up-river, where our boardwalk passes over wetlands to our pier and offers an open view both up and down the river.

Chestertown Tea Party Festival

In May 1774, five months after the British closed the port of Boston following the Boston Tea Party, the citizens of Chestertown wrote a set of resolves that prohibited the buying, selling, or drinking of tea. Based on these resolves, a popular legend originated purporting that the Chestertown citizens held heir own "tea party" on the Chester River in Chestertown, in an act of colonial defiance. The Chestertown Tea Party Festival today celebrates Chestertown's colonial heritage with a weekend of events including a re-enactment of the legendary "tea party."

Schooner Sultana

The Schooner Sultana is a reproduction of the British Navy ship the HMS Sultana. Over 3,000 students participated in the community and educationally led effort to build the replica, with a core group of volunteers logging over 150,000 hours of time. The ship was launched in March 2001 and is based in Chestertown, MD. Various educational and leisure activities are available onboard.


Chestertown is home to Washington College, a private liberal arts college founded in 1782. Washington College is the tenth oldest college in the USA. George Washington was a founding patron and provided the college with a small endowment. The college is known nationally as the home of the Sophie Kerr Prize, which is awarded to the graduating senior with the most literary potential.

Perhaps the most direct benefit to our residents is the Washington College Academy of Lifelong Learning, or WC-ALL. It offers a wide variety of courses in which many of our residents enroll, and some serve as instructors. Concerts, films, and student plays, as well as lectures by well-known personalities, are offered by the college each year and add to the many opportunities available to Heron Point residents. Additionally, some residents choose to audit selected college courses for a matriculation fee.

Chestertown Farmers' Market and Artisans' Market

Every Saturday morning from April to December in downtown Chestertown, home-grown produce and home-made products are available for sale at the Farmers' Market. Nearby, the Artisans' Market provides a venue for artists to display and sell an array of Eastern Shore art produced by local artists, painted furniture, beach glass, pottery, unique jewelry, photography, and more.

Convenience and Surrounding Area

Nothing is far away in Chestertown. Both the hospital and Washington College, for example, are a half-mile or less from Heron Point and all local shopping is within two miles.

Whenever residents wish to be on the go, there are a wealth of things to do in the area around Chestertown, including:

  • Rock Hall, one of the largest boating centers on the Chesapeake Bay
  • Eastern Neck National Wildlife Refuge
  • Rock Hall Yacht Club
  • Chester River Yacht and Country Club

For more information about the area visit Chestertown.com.