Discover Chestertown’s

Parks & Playgrounds

Wilmer Park

Ajax Park

Fountain Park

Gateway Park

Kent County Middle School

Louisa d’Andelot Carpenter Park

Margo G. Bailey Park

Memorial Park

Remembrance Park


Stetson Dog Park


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!