Chestertown on the Chester River: History and Culture

Chestertown lies on the banks of the Chester River. If you’re looking for a hotel in Chestertown, you can plan your trip around history, exhibitions, walks, or activities connected with the river. The Chestertown Historic District is designated a National Historic Landmark and was listed on April 15, 1970. Tours, college visits, and outdoor trails offer different ways to explore the area.

Historic District and Local History

A self-guided walking tour of Chestertown’s Historic District includes 29 stops. You can follow the route independently and explore the various sites in the historic district. Guided walks are also available for groups of five or more; they must be reserved at least two weeks in advance. As booking requirements may change, check the provider’s requirements before planning a group visit.

Chestertown’s Arts & Entertainment District covers 51 acres of the historic downtown. It stretches from the banks of the Chester River to Mill Street. Washington College adds its own history to the area: founded in 1782, it was the first college to receive a charter in the sovereign United States of America. Visits may include a campus tour with a current student and a one-on-one conversation with an admissions counselor. Visit arrangements may change, so check the planned activities before making plans.

College, Exhibitions, and Chesapeake History

Visitors to the Bordley History Center can explore rotating museum exhibitions about local industries, preservation efforts, African American history, and notable residents of Kent County. MuSE is a public exhibition space in downtown Chestertown featuring rotating exhibitions on teaching, experiential learning, and research at Washington College. The two venues focus on different topics: the Bordley History Center covers local and regional history, while MuSE focuses on learning and research at the college.

The Schooner SULTANA is a full-scale reproduction of a 1768 British Royal Navy schooner. Its educational programs offer hands-on exploration of the ecology, wildlife, and human history of the Chesapeake Bay watershed. A description last updated on September 19, 2025, names Chestertown’s historic port as one of SULTANA’s departure points; it also sails from other locations on the Chesapeake Bay. If you’re planning a voyage, check the current schedule.

River Cruises and Events

The 2026 schedule lists regularly scheduled public cruises aboard the River Packet from April through November. Seasonal schedules may change, so check the specific dates for your stay. The Chestertown Tea Party Festival also has a set annual date: it takes place over Memorial Day weekend. When planning, refer to that year’s festival dates.

Outdoor Trails and Practical Information

The two-mile Wayne Gilchrist Trail follows a former railroad line that has since been paved. It offers a scenic, protected route for walking or cycling. This gives you a specific outdoor activity to add to a stay focused mainly on exhibitions and history.

The Chestertown Visitor's Center provides maps, brochures, and insider tips, and offers information about restaurants, shopping, events, and attractions. Opening arrangements may change, so check visitor details in advance. This way, you can plan around the topics that interest you and make note of important dates or reservations in good time.

Discover more destinations: Massey, Rock Hall.

View the broader travel overview: Kent County.