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    Eastern Shore Life at its Best

    Main Street Historic Chestertown Inc. is a 501(c)3 non-profit organization which is dedicated to preserving, enhancing, and promoting historic downtown Chestertown, Maryland. Chestertown is located on Maryland’s Eastern Shore on the banks of the Chester River. Established in 1706, this small colonial town encompasses the arts, the environment, and history. Come experience Eastern Shore life at its best!

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    Featured Business

    Coco’s Pet Center

    Shop for your favorite furry friend!

    Coco’s Pet Center is dedicated to providing unique, handmade, fun pet supplies that will make your pet’s life a bit brighter! 

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    The Chestertown Chat

    Follow our Chestertown blog to hear from visitors and residents who love our colonial town.
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    Explore Downtown Chestertown

    Plan your trip to downtown Chestertown and see all that you can do within walking distance.

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    • Download Walking Map

    Trip-Planning Resources:

    Kent County Visitors Center

    Bordley History Center

    Washington College

    The Sultana Education Center

    Sumner Hall

    Main Street Rock Hall

    Kent County Parks & Recreation

    and more….

    Main Street Chestertown would not be possible without the support of our partners: