Chestertown’s past as a Colonial port is very much in evidence today. The consolidated, dense downtown exudes history. In fact, the town features one of the largest collections of 18th- and 19th-century structures in Maryland, second only to Annapolis. Founded in 1706, Chestertown was the geographic center of population in the United States by 1790. After it was named one of six Royal Ports of Entry in Maryland, the influx of money allowed merchants to build large, attractive homes along the river. Money was made in tobacco, then in shipping grain to the West Indies and in shipbuilding. Before the Revolution, trade with the West Indies was hampered by English taxes, resulting in Chestertown’s own Tea Party in 1774, when a small cargo of tea was tossed into the Chester River. The event is reenacted annually on Saturday of Memorial Day weekend during a weekend-long celebration.
In 1782, Washington College–the 10th oldest liberal arts college in the country–was founded here. Visit the campus to explore the Georgian architecture of the buildings. (Transportation required.)
Chestertown hosts many festivals and events throughout the year including the Chestertown Tea Party Festival in May, the Sultana Downrigging Festival in October and RiverFest in September.
The Waterway Guide Team has gained extensive boating knowledge over the years, and now we are sharing all of the tips, skills and tools we’ve picked up along the way!