DCA  Sponsored  Annual  Events

First Friday (Year-round)

First Fridays are held on the first Friday of every month. Enjoy extended shop hours, art gallery openings, restaurant specials and entertainment while meandering the red-brick, tree-lined sidewalks of Historic Chestertown.

Taste of the Town (April)

Spend an afternoon on the bank of the Chester River sampling signature dishes from Chestertown’s finest restaurants and caterers. Featured dishes range from nouvelle gourmet to regional classics such as Maryland Crab Soup.

Independents' Day Celebration (July's First Friday)  

Old-Fashioned family fun with live music, cotton candy, sno cones, corn dogs in Fountain Park - 5:00 - 8:00pm

Crazy Days Summer Sidewalk Sale (July 28, 29,30)

Not just your average sidewalk sale. Downtown's famous Crazy Days sale is held once a year (Usually the end of July) in the historic district. It’s easy to find fabulous bargains as local shops display sale items on the red-brick sidewalks of Chestertown.

Holiday Lights & Winterfest Weekend (Nov/Dec)

An entire weekend filled with holiday events - The official lighting of Downtown for the holidays, Kent County Marching Band, the arrival of Santa and caroling in Fountain Park. Downtown stores have extended hours throughout the weekend.