Main Street Chestertown is Hiring!
Main Street is currently seeking a new full-time Executive Director to begin immediately. For more information and to apply, click the button below
Hometown Holiday
November 29
Kick off the Holiday Season with one of Downtown Chestertowns most iconic events, the arrival of Santa and Mrs. Clause on a fire truck! Enjoy the festive holiday music, candy, and some of the most iconic characters of the holiday season enjoying the downtown.
