ABOUT
EASTERN SHORE LIFE AT ITS BEST
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
Discover unique treasures, household goods, and much more with our locally owned downtown shops.
DINING
From artisan pizza, award winning Maryland crab cakes, and so much more, Chestertown's downtown dining always hits the spot.
EXPERIENCES
Experience everything Chestertown and Kent County has to offfer from lectures at Washington College to kayaking the Chester River.
ACCOMMODATIONS
Downtown Chestertown offers many choices for our out of town visitors, including a newly renovated downton inn, classic Bed and Breakfasts, and many Air BnB's. .
SERVICES
Explore the many services Chestertown and Kent County have to offer.
EVENTS
From our Signature Events like the Chestertown Tea Party and Dickens Festival to recurring events like First Friday, Chestertown is a great weekend getaway.
THE CHESTERTOWN CHAT
Experience Chestertown’s colonial charm through our dedicated blog. Join us as we bring you firsthand accounts from enthusiastic visitors and passionate residents who have fallen in love with our historic town. Discover the hidden gems, explore the rich heritage, and immerse yourself in the stories that make Chestertown truly special. Stay connected and be inspired by the captivating narratives that unfold on our Chestertown Chat!
UPCOMING EVENTS
Chestertown is known for some long standing popular events that draw visitors from around the world! Enjoy Chestertown's year-round festivities from the weekly Farmers' Market to our Dickens of a Christmas in December! Join us for our next event, we promise good entertainment, good refreshments and great people!
UPCOMING SIGNATURE EVENTS
Chestertown, Maryland was founded in 1706. It was established as a port town and played a significant role in the colonial era, serving as a bustling trade hub along the Chester River. Today, Chestertown retains much of its historic charm and is known for its well-preserved 18th-century architecture and vibrant cultural scene. Thanks for checking us out!
office@mainstreetchestertown.org
(410) 778-2991
OFFICE
Chestertown Town Hall
118 N. Cross Street
Chestertown MD 21620
MAILING ADDRESS
PO Box 427
Chestertown MD 21620
Main Street Chestertown would not be possible without the support of our partners:
