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

Featured Business

Coco’s Pet Center

Shop for your favorite furry friend!

Coco’s Pet Center is dedicated to providing unique, handmade, fun pet supplies that will make your pet’s life a bit brighter! 

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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