Chestertown lies on the banks of the Chester River. History, exhibits, trails, and boating experiences offer different ways to shape your stay. At the heart of it all is the Chestertown Historic District: explore it on a self-guided tour, learn about the history of Washington College, or discover other cultural topics through exhibits.
Historic District and Walks
The Chestertown Historic District is a National Historic Landmark; it was listed on April 15, 1970. Chestertown’s Arts & Entertainment District covers 51 acres of the historic downtown and stretches from the banks of the Chester River to Mill Street. These details give the historic area a clear geographic frame of reference.
The self-guided walking tour of the Historic District includes 29 stops. You can take the tour on your own, focusing on each stop along the way. Guided walks through the district are available for groups of five or more and must be reserved at least two weeks in advance. For planning purposes, the main consideration is whether you prefer a self-guided tour or would like to reserve a guided tour with a group.
History, Exhibits, and Education
Washington College was founded in 1782 and was the first college to receive a charter in the sovereign United States of America. Its founding story offers a distinct way to explore local history. Those considering the college as a possible place to study can also plan a visit, which may include a campus tour with a current student and a one-on-one meeting with an admissions counselor.
At the Bordley History Center, visitors can view changing museum exhibits on local industries, preservation efforts, African American history, and notable residents of Kent County. MuSE has a different focus: its public exhibition space downtown features changing exhibits on teaching, experiential learning, and research at Washington College. Together, local history and college-related themes offer distinct cultural perspectives.
Ships and the Chester River
The schooner SULTANA is a full-scale reproduction of a 1768 British Royal Navy schooner. It sails from Chestertown’s historic port. Its educational programs offer a hands-on look at the ecology, wildlife, and human history of the Chesapeake Bay watershed. This connects the ship’s historical context with topics related to the Bay.
In 2026, the River Packet offers regularly scheduled public cruises from April through November. If you’d like to include a cruise in your plans, check the schedule for your preferred date, as seasonal schedules can change. The Chestertown Tea Party Festival takes place annually on Memorial Day weekend; check the specific event dates if you’re planning to visit for the festival.
Another Outdoor Option
The two-mile Wayne Gilchrist Trail follows a former railroad corridor that has since been paved. It offers a scenic, protected route for walking or cycling. This makes it different from the stop-focused walking tour of the Historic District: the trail is primarily a route for walking or cycling. The two options therefore appeal to different interests, so you don’t have to limit yourself to just one way of getting around.
Plan Your Visit
The Chestertown Visitor’s Center provides maps, brochures, and insider tips, as well as information about restaurants, shopping, events, and attractions. Since visitor arrangements can change, check current opening hours before stopping by. If a visit to Washington College is relevant to your travel plans, you can also find out about visiting options in advance; specific offerings may change.
Discover more destinations: Massey, Rock Hall.
For the broader travel overview: Kent County.
