Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.

The second annual Carnival on High will be held Saturday, July 1 from 5-8pm at the Foot of High Street. This year will include more face painters, more games, and a bubble performer. Bring the whole neighborhood and enjoy a summer favorite! This event is free and open to the public. All proceeds benefit Main… Continue Reading Carnival on High

Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.

Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.

Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.

Your favorite annual car show is back! Enter your car to be judged or come view over 100 antique, classic, and modern cars on display in downtown Chestertown. Live band, food, and more. This event is free and open to the public. All proceeds benefit Main Street Chestertown.

Join Main Street Chestertown for Cars on High every third Thursday (April through October). Share your automotive beauty or come drool over someone else's! This event is free and open to the public.