[4][5] Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry.

[7] A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprang up along the waterfront.

25, Grand Army of the Republic, Thornton, Washington College: Middle, East and West Halls, and White House Farm (Chestertown, Maryland) are listed on the National Register of Historic Places.

Based on these resolutions, a popular legend has it that the citizens held their own "tea party" on the Chester River in an act of colonial defiance.

A parade begins the festival, marching down High Street to the Chester River, and then follows with colonial music and dance, fife and drum performances, puppet shows, colonial crafts demonstrations and sales, military drills, and a walking tour of the historic district.

In 1997, John Swain came up with blueprints for a reproduction of the American-built yacht, later Royal Navy schooner HMS Sultana, planning the construction and home of the ship to be centered in Chestertown.

In the same year the non-profit group Sultana Projects, Inc. was formed by Swain and supporters to fund construction of the ship.

Over 3,000 students participated in the community and educationally led effort, with a core group of volunteers logging over 150,000 hours of time building the ship.

The Sultana also plays a key role in the Chestertown Tea Party, as it is now the official boat of the staged re-enactment.

Chestertown was selected from 63 destinations in 27 states that were nominated by individuals, preservation organizations, and local communities.

In 2008, Progressive Farmer magazine honored Kent County and Chestertown by naming it #1 in "Best Rural Places to Live in America".

"For a county to be in Progressive Farmer's Best Places list, they hold them to the usual standards — good schools, health care, safety and other desirable qualities.

[citation needed] 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.

Maryland Route 213 is the most significant highway serving the town, and is the main north–south road along the eastern shore of the Chesapeake Bay.