Donate
    Donate

    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!

    Shopping

    Dining

    Experiences

    Main Street is Hiring!

    Main Street Chestertown is currently seeking a part time assistant director to help facilitate our work of helping Chestertown to thrive. For a full description and details about applying, click below. Applications will be accepted until February 28. (The picture of Keke the Cat is just because she's cute.)

    Assistant Director Job Posting

    Stay up to date on all things Main Street Chestertown by signing up for our quarterly newsletter!

    Subscribe

    * indicates required

    Upcoming Events

    View All Events

    Featured Business

    Bespoke Chocolates

    Welcome to one of our newest businesses!

    Bespoke Chocolate is your destination in Chestertown for chocolate and other sweet treats! Plus: Special events, custom chocolate designs, and more.

    Visit Their Page

    The Chestertown Chat

    Follow our Chestertown blog to hear from visitors and residents who love our colonial town.
    More Posts

    Explore Downtown Chestertown

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

    Filters Filters
    arrow_backward
    arrow_forward
  • There are no listings matching your search. Reset Filters

    • 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: