2026 Chestertown Holiday Parade

Chestertown’s holiday season officially kicks off on Friday evening, November 27, 2026, with Hometown Holiday and the Annual Chestertown Holiday Parade. The parade begins at 5:30 p.m. on High Street and features marching bands, classic automobiles, festive floats, and family fun for all ages. Parade judges will award cash prizes to entrants in each category, and participation is open to everyone. Businesses, organizations, community groups, and individuals interested in entering a float or group are encouraged to participate. To register, please email downtownchestertown@gmail.com. Santa Claus is expected to make his grand arrival by fire truck as part of the parade festivities. Following the parade, families can enjoy opportunities to visit with Santa and share their holiday wishes.