Located on the banks of the Chester River, the historic town of Chestertown is the county seat of Kent County, MD and was once a thriving port of entry for Colonial settlers into Maryland, Chestertown has an abundance of beautifully restored 18th-century homes, lovely churches and several interesting shops within walking distance of the town wharf. 
 
Chestertown's shipbuilding past has been revived by the recent Schooner Sultana project.  The Sultana, a replica of a traditional 18th century schooner, was constructed locally by a non-profit organization using traditional ship building skills and launched in May of 2001. 

Chestertown is located about 25 miles up the Chester River from its mouth. Although long, the passage form the Chesapeake Bay to Chestertown is well marked and the channel is wide and deep. The only bridge to get in your way is the 12-foot closed vertical clearance bascule bridge just beyond the Chestertown waterfront.

Chestertown was chartered in 1706 as a town by the Maryland Assembly’s “Act for the advancement of trade and erecting ports and towns in the Province of Maryland.” Almost one hundred acres were purchased from Simon Wilmer who held one of the original land grants.

Along with being a trade center, Chestertown rapidly became a center for government, court and higher education. The town is home to Washington College, founded in 1782.  It is the 10th oldest Liberal Arts college in the United States. The County’s court records, dating back to the 1640s, are the oldest in the State. Colonial justice, less codified then it is today, listed “repairing bridges” as one of the more popular sentences for those convicted of minor crimes. In the 1650s a court record reports a suspected cattle rustler was sentenced to be forbidden to go into the woods unless accompanied by “2 honest neighbors.”

Today, Chestertown is the county seat and the focal point of most community activities relating to the entire county. Its historic district, well preserved for the enjoyment of both residents and tourists, draws visitors from across the country who participate in activities ranging from antiquing to boating to golfing to shopping and touring old homes.

Chestertown is located up the Chester River about 25 miles form the Chesapeake Bay. From the Chesapeake, find the Love Point Light marking the Love Point Shoal northeast of the actual point itself. From here, there are a series of nun buoys, lighted buoys and fixed aids to navigation, most of which mark shoals extending into the river from shore.

See the Calendar of Events in the “Helpful Links” section below.

Most everything in Chestertown is within walking distance, or easily reachable on a bike. From the downtown marina there are several shops set in a Main Street-style setting. Chestertown is rural and access to major airports is limited to Baltimore and Philadelphia; both a major trek from Chestertown.

City of Chestertown

Kent County Chamber of Commerce

Kent County Calendar of Events