Chestertown, Maryland

Eastern Shore Life At Its Best


Things to Do

Plan Your Visit

Events Calendar

Rich in History.
Rooted in Community.

Chestertown Marina with the Sultana docked

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.

Happy Anniversary, Goddess Hebe!

Fountain Park, in the center of Chestertown, is located at the corner of High and Cross Streets. The centerpiece fountain, “Lady in the Park”, topped with the Greek goddess of youth Hebe, was cast in the late-1800’s in Philadelphia by Robert Wood and Company  sometime between 1866 and 1878. It has been a Chestertown landmark since 1899, when the Ladies Improvement Society, later to become the Chestertown Garden Club, purchased it from a park in Wilmington. This year, the Fountain will celebrate its 125th Anniversary in early August with an event in the Park. 

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!

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

Child looking outside the shop in downtown Chestertown


Discover unique treasures, household goods, and much more with our locally owned downtown shops.

Customers dining outside in front of the Kitchen in Chestertown, Maryland under an umbrella table


From artisan pizza, award winning Maryland crab cakes, and so much more, Chestertown's downtown dining always hits the spot.


Experience everything Chestertown and Kent County has to offfer from lectures at Washington College to kayaking the Chester River.

Front of The White Swan Tavern Downtown Chestertown


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. .


Explore the many services Chestertown and Kent County have to offer.


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

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