Welcome to Chestertown

Local Attractions and History

Chestertown, established in 1706, was once an important seaport during the colonial period and is now the county seat of Kent County. Chestertown is not a town that history forgot; instead, it is a town that history gratefully remembers. Proud of their colonial past, residents have restored many of the Georgian and Federal homes built during the 18th century by wealthy merchants. The White Swan is one of many historic buildings that makes up the architecturally interesting downtown! Be sure to grab the walking tour guide at the front desk. See the About Us page for more history about the restoration and history of The White Swan.

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Events & Local Activities

There is always something happening here in Chestertown. Check the links below to see what’s going on during your stay!

There are many interesting things to do and see in the area, as well as unique shopping and terrific restaurants. Chestertown is home to Washington College, the tenth-oldest college in the nation. The quiet pace of the Eastern Shore makes for a wonderful retreat whether you are a boating enthusiast, a cyclist eager to enjoy some of the best bike riding in the region, a kayaker looking to explore the many waterways in the area, a lover of college sports or someone who simply wants to enjoy a good book curled up here in the cozy inn.