Main Street Historic Chestertown, Inc. is a 501(c)(3) non-profit organization dedicated to preserving, enhancing, and promoting the historic downtown of Chestertown, Maryland. Located on the banks of the Chester River, this small colonial town offers a unique blend of arts, environment, and history, providing visitors with an authentic Eastern Shore experience.
From locally owned downtown shops offering unique treasures to a diverse dining scene that includes award-winning Maryland crab cakes, Chestertown offers a range of experiences for visitors. With accommodations ranging from a newly renovated downtown inn to classic Bed and Breakfasts and Airbnbs, visitors can immerse themselves in the rich heritage and hidden gems of this charming town.
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