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!


Friday, July 1 5-8pm

Join Main Street during July’s First Friday for a carnival! Attractions will include a trackless train, face painting and balloon animals, games & prizes, a magician and more! For more details, click on the image to the left. See you on the midway!




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.

Upcoming Events

Carnival on High

Friday, July 1, 5-8pm Bring the kids or relive your own childhood with Main Street's Carnival on High. Attractions include a train, face painting, food, and more!

Explore Downtown Chestertown

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

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