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!




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.)

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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.

The Chestertown Chat

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

Explore Downtown Chestertown

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

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