Plan A Visit


Plan your trip to Chestertown with these three trip itineraries!

GET OUTSIDE: Suggestions for outdoorsy types

Throw the kayaks or bikes on the car and escape to Chestertown and the surrounding county—full of gorgeous Chesapeake landscapes, secluded waterways, and hikes.  Chestertown is the perfect launch site for all kinds of outdoors adventures—and a great place to rest, relax and fuel up for your next day on the river or trail.

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LOCAL FLAVOR: A taste experience for foodies 

For unabashed foodies, Chestertown has a lot to offer. From the award-winning farmer’s market to local shops stocking fine wines, locally distilled liquors, imported cheeses and locally aged beef, culinary adventures await in the historic downtown and surrounding Kent County countryside.

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PAST IS PRESENT: Exploring a sense of place and history. 

In a town with a rich past and so many extant historic buildings, Chestertown has long been a draw for history lovers of all ages. From its brick cobbled sidewalks to its impressive colonial waterfront mansions, Chestertown’s history is a big part of what makes it unique—and also makes it the perfect getaway for history buffs. Over 300 years, Chestertown has seen great changes—and many of its buildings, museums, and civic spaces tell fascinating stories about how national, regional, and local events shaped the community over time.

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