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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!




Featured Business

Bee Crafty Collectibles

Bee Crafty recently celebrated their 5th anniversary! This diverse and eclectic shop features home decor, handmade signs, furniture, and more. Check out their amazing shop on High Street!

The Chestertown Chat

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

The Rest of the Story

This article is from the October 2021 issue of Chesapeake Bay Magazine, written by Rafael Alverez, a writer sponsored by Main Street Chestertown. Emily Kalwaitis,

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Upcoming Events


Thank you to all of the volunteers, sponsors, vendors, and performers who helped to make Dickens 2021 such a special event. A special THANK YOU to the amazing crowd who came out en force to celebrate the holiday season, Dickens-style. We can't wait to see you next year!

Explore Downtown Chestertown

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

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