First Friday – December 6, 2019

First Friday – December 6, 2019

First Friday is always a great time in Chestertown! If you're looking for all of the Dickens of a Christmas happenings, click here. Many of our shops and businesses will be open late downtown, with special promotions and events planned. You'll find that info here. 
First Friday – Nov 1, 2019

First Friday – Nov 1, 2019

First Friday is always a great time in Chestertown! This month, there is even more to do as we celebrate the Downrigging and Bluegrass Festival. Many of our shops and businesses will be open late downtown, with special promotions and events planned. This is a 
First Annual Chestertown Car Show

First Annual Chestertown Car Show

Saturday, September 14 from 2:00-6:00 PM Fountain Park, Chestertown For more info or to register a vehicle, visit chestertowncarshow.com.