Founded in 1706, Chestertown is a historic college town along the banks of the Chester River on Maryland's Eastern Shore. The brick sidewalks lined with shops, restaurants and inns welcome visitors to meander and browse. A visit to Chestertown's Historic District to admire the fine colonial residences is a must!.
2 Annual Festivals and Events
Experience Chestertown like a local by attending one of the many unique annual events. During Memorial Day weekend there is the annual Chestertown Tea Party Festival and don't miss the Pirates and Wenches Fantasy Weekend in August - but no matter what time of year you visit, you can count on an entertaining event or festival.
3 The Garfield Center for the Arts at the Prince Theatre
The Garfield shakes-up the cultural life of Chestertown with great programming that nurtures and celebrates arts and artists - essential elements of life in Chestertown.
Serving as Kent County's seat of government since 1706, Chestertown has been a Royal Point of Entry, the scene of its own Revolutionary Tea Party in 1774, and the hub of a bustling agricultural and seafood region. The Historical Society of Kent County is a treasure trove of history and offers a great self-guided walking tour you can access via your smartphone.
More about Historical Society of Kent County
301 High St
Chestertown, MD 21620
6 Washington College
Founded in 1782, Washington College was the first college chartered in the sovereign United States of America. General George Washington lent his name, donated 50 guineas to the founding, and served on the first Board. The mission back then was to cultivate responsible citizen-leaders. Nowadays, the focus is on giving students the chance to succeed on their own terms.
7 Scooner Sultana
The Sultana connects people to the Chesapeake Bay’s history, ecology, and culture, inspiring all to be a part of preserving and restoring America’s largest estuary.
Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival has evolved into one of the largest annual Tall Ship gatherings on the East Coast.
More about Sultana Education Foundation
200 S. Cross St
Chestertown, MD 21620