Chestertown, Maryland
Eastern Shore Life At Its Best
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Rich in History.
Rooted in Community.
Voted The Best Small Town in Maryland to Chill Out
Immerse yourself in our rich history as you stroll down brick-lined streets, lined with 18th-century homes and historic landmarks. Explore our bustling arts scene, with galleries and studios showcasing local talent. Indulge in fresh, local cuisine at our quaint cafes and restaurants, or take a scenic cruise along the Chester River.
Whether you’re seeking a weekend getaway or a leisurely vacation, Chestertown offers a charming retreat for every traveler.
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!
Don't Keep it a Secret!
Share your upcoming event with the community!
Downtown Chestertown
Dive into downtown Chestertown’s charm, boasting over 200 specialty shops, art galleries, restaurants, bars, and more. Discover the vibrant heart of our town!
Visitors Center
Discover the insider knowledge on where to find the best cream of crab soup in town, indulge in the tastiest ice cream, and plan your visit to the art galleries. Let us guide you to create a spectacular experience in Chestertown that combines culinary delights, sweet treats, and a journey through the town’s vibrant art scene.
Things to Do
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.
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Your Guide to Chestertown
Latest News
Main Street Welcomes New Executive Director, Sonia “Sonny” Huntzinger
November 4, 2024 - Chestertown, MD — Main Street Chestertown is thrilled to announce the appointment of Sonia "Sonny" Huntzinger as its new Executive Director. With over two decades of experience in...
Companion Cities: Chestertown
In case you were wondering why there is a Canadian flag flying in front of the Chestertown Maryland Town Hall.....here’s how it came to be. Since 1987 Chestertown, Maryland has been the Companion...
Downtown Master Plan Release
Press Release March 25, 2024 Main Street Chestertown and local partners are embarking on a Downtown Master Plan with Design Collective, Inc., a Baltimore-based consulting firm, to envision the...