Lifestyle May 8, 2023

Chestertown, MD: Embracing History, Culture, and Natural Beauty in a Charming Small Town

This week’s community profile we are focusing on Chestertown, Maryland – a charming, historic town situated on the banks of the Chester River in the Eastern Shore region of Maryland. With a population of just under 5,000 people, Chestertown offers a unique blend of small-town charm and modern amenities, making it an attractive location for  visitors and prospective residents.


Chestertown has a rich history dating back to its founding in 1706. As one of Maryland’s oldest towns, it played a significant role in the American Revolution and was a center of commerce and trade during the 18th and 19th centuries. Today, visitors can explore Chestertown’s historic district, which features more than 300 18th-century buildings, including the 1769 courthouse where George Washington once visited.

Arts & Shops

In addition to its historical significance, Chestertown offers a variety of modern amenities, including shops, restaurants, and cultural attractions. The town is home to several art galleries, including the Massoni Gallery and the River Arts Gallery, as well as the Garfield Center for the Arts, which hosts plays, concerts, and other performances throughout the year.

Parks and Outdoors

For outdoor enthusiasts, Chestertown offers a variety of recreational opportunities, including fishing and boating on the Chester River and hiking and biking on the nearby  Rail Trail. The town is also home to Wilmer Park, a popular destination for picnics, concerts, and other outdoor events.

Higher Education

Education is also a highlight of the Chestertown community. The town is home to Washington College, a private liberal arts college founded in 1782. The college offers undergraduate programs in a variety of fields, including environmental science, creative writing, and business management. In addition, the Sultana Education Foundation offers a variety of educational programs for students of all ages, including field trips, summer camps, and sailing adventures on the Chester River.

Festivals & Events

Chestertown is a town that loves to celebrate its history, culture, and natural beauty through a wide variety of events and festivals held throughout the year. One of the most popular events is the Chestertown Tea Party Festival, held annually in May to commemorate the town’s colonial heritage and resistance to British rule. This festival includes reenactments, live music, food and craft vendors, and a parade. Another popular event is the Sultana Downrigging Weekend, a maritime festival held in October featuring tall ships and historic vessels. Throughout the year, Chestertown also hosts a variety of concerts, art shows, and community gatherings, such as the weekly farmers market and the First Fridays events in the historic district. No matter what your interests, there’s always something to see and do in Chestertown.


If you’re considering a move or visit to Chestertown, there are several resources that can help you get acclimated to the community. Here are a few links to get you started:

  • Town of Chestertown Website: The official website of Chestertown provides information on local government services, events, and news. You can also find information on utilities, permits, and other important services.
  • Kent County Maryland Website: The Kent County website is filled with information and resources for the county’s visitors, residents and business.  This site also houses information about the surrounding areas and local government.  
  • Main Street Chestertown: As a Main Street community, we’re part of a national network of historic downtowns created by the National Trust for Historic Preservation. Our 501(c)(3) nonprofit is guided by the Trust’s tested model for revitalization as we work to improve streetscapes, support our unique shops and restaurants, attract new ones, and create fun events that draw people downtown.
  • Sultana Education Foundation: This nonprofit organization offers educational programs focused on the history and ecology of the Chesapeake Bay region, including opportunities for kayaking and sailing on the Chester River.
  • Garfield Center for the Arts: This performing arts center hosts a variety of concerts, plays, and other performances throughout the year.

Visit our website, to find your Chestertown dream home or stop by our Coldwell Banker Chesapeake office located at 114 S. Cross Street, Chestertown, MD 21620.  Our agents provide themselves in their community involvement and expertise on Chestertown and the surrounding Kent & Queen Anne’s County areas.