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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

Twigs & Teacups

Twigs & Teacups has been a fixture in Chestertown for over 30 years. With just a hint of nostalgia and a world of possibilities, their shelves hold a selection of gifts for every important person in your life, including friends, family, and, of course, yourself. 

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

A Dickens of a Christmas 2021

This holiday favorite is back! Join us downtown December 3-5 for a Dickens of a good time. Some familiar faces are returning, such as the internationally renowned American Rogues. Some new events have been added, such as pony rides and a petting zoo. To learn more, click the title above. Come celebrate like it's 1840!

Explore Downtown Chestertown

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

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