Chestertown: History, River, and Special Discoveries

Chestertown combines historic discoveries with the character of a river town on the Chester River. At its heart is the Chestertown Historic District, which was listed as a National Historic Landmark on April 15, 1970. There are also museums, exhibitions, walking and cycling trails, and maritime experiences, allowing you to shape your trip in many different ways: around cultural history, active exploration on foot or by bicycle, or maritime experiences.

Discover History on Your Own or with a Guide

A self-guided walking tour through Chestertown's Historic District includes 29 stops. It allows you to organize historical impressions independently and fit the tour into your personal daily schedule. If you prefer an introduction with a guide, you can reserve a guided tour for a group of five or more people. Registration is required at least two weeks in advance.

Washington College also shapes the town's historic character. It was founded in 1782 and 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 personal conversation with an admissions counselor. For orientation in the area, the Chestertown Visitor's Center provides maps, brochures, and insider tips and offers information about restaurants, shopping, events, and attractions.

The Bordley History Center and the city's exhibition venues offer further insights. At the Bordley History Center, visitors can see changing museum exhibitions on local industries, preservation efforts, African American history, and notable residents of Kent County. Chestertown's Arts & Entertainment District covers 51 acres of the historic town center and extends from the Chester River waterfront to Mill Street. MuSE is a public exhibition space downtown with changing presentations on teaching, experiential learning, and research at Washington College. The Chestertown Decoy Museum seeks to preserve for the public the historical and artistic heritage of decoy figures and their carvers, with a particular focus on the Chesapeake region and beyond.

River, Trails, and Maritime Experiences

The Chester River is not only part of the town's setting but also provides the backdrop for a variety of travel experiences. The Schooner SULTANA is a full-scale reproduction of a 1768 British Royal Navy schooner and sets sail from Chestertown's historic harbor. Its educational programs explore the ecology, wildlife, and human history of the Chesapeake Bay watershed through hands-on activities. During the Sultana Public Sails on August 14, 2026, the cruise lasted two hours. Passengers could help set the sails, steer with the seven-foot oar, and explore the authentically recreated crew quarters below deck.

Another way to experience the river area is the River Packet, which offers regularly scheduled public cruises from April through November. The two-mile Wayne Gilchrist Trail follows a former railroad line that has since been paved. The scenic, protected path is well suited to planning days around hiking or cycling and offers a different focus from a day spent visiting museums, the campus, and historic sites.

Market, Traditions, and Finding the Right Accommodation

The Chestertown Farmers and Artisans Market takes place year-round on Saturdays and adds a regular weekly event to the cultural offerings. Another special tradition is the Chestertown Tea Party Festival, held annually over Memorial Day weekend. If you are looking for a vacation rental or vacation home in Chestertown, you can first decide which of these experiences should be the focus of your stay. For a culture-focused trip, the Historic District, college, exhibitions, and guided tours take center stage; for more active days, the Wayne Gilchrist Trail and the activities on the water are additional options.

More Travel Ideas

For additional travel ideas, you can also view Massey and Rock Hall.

To the overarching travel overview: Kent County.