The Chestertown Car Show will cruise into the heart of downtown Chestertown on Saturday, October 2 from 2:00 to 6:00 p.m., complete with judges’ awards and a beverage tent.
Main Street Chestertown Welcomes Nina Fleegle as New Executive Director
Street Party with a Motown Mix to Introduce Chestertown's New Mobile Stage May 29th
Main Street Chestertown will officially launch Chestertown’s new mobile stage on the Saturday of Memorial Day Weekend, May 29, with a street party featuring the popular band Best Kept Soul. The free event will kick off at noon in the 200 block of High Street, where members of the Town’s Street Department will have set up the stage in public for the first time.
Chestertown A&E District Hosts Art Walk April 24
Live music will enliven the sidewalks Saturday, April 24 as The Chestertown Arts and Entertainment District hosts a Spring Art Walk to a dozen downtown galleries and studios. The event takes place from 10 a.m. to 4:00 p.m. The theme of the Art Walk is “Re-emergence,” a reference to both the natural world awakening to Spring and the world’s eagerness to emerge safely after a winter of pandemic isolation.
