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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!


Wilmer Park Playground

We Did It!

Thanks to the incredible generosity of our community near and far, we reached our goal! We can’t thank you enough for the tremendous support that will bring a safe and accommodating play space to our beloved Wilmer Park. Stay tuned for more improvements to come, including landscaping and benches. A special thanks to the Recreation Commission for their tireless work.




Featured Business

Tiny Tots Boutique

Happy 5th Anniversary to Tiny Tots Boutique! 

Tiny Tots Boutique carries kids’ apparel that is original, trendy, and made with active boys and girls in mind. We have great gifts for newborns & toddlers.

The Chestertown Chat

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

God Bless Us (and everyone)

God Bless Chestertown (and everyone)  by Rafael Alvarez  As the circus proprietor Sleary declares in the Charles Dickens’ novel Hard Times, “People must be amused

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The Rest of the Story

This article is from the October 2021 issue of Chesapeake Bay Magazine, written by Rafael Alverez. Emily Kalwaitis, bookshop manager at The Bookplate in Chestertown,

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Upcoming Events

Tea Party Is Back!

Join the Revolution May 27-29! In response to British Parliament’s closing of the port of Boston, the citizens of Chestertown, Maryland met in May of 1774 and set forth “Resolves” forbidding importing, selling, or consuming tea in Chestertown. The annual reenactment of tossing The Tea Overboard is the centerpiece of the Chestertown Tea Party Festival. Fun for everyone! Colonial artisan vendors, music, children's activities, Sunday's beer tasting & the fabulous raft race. New this year- Saturday Fireworks!

Explore Downtown Chestertown

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

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