This series of gatherings takes place in downtown Chestertown every third Thursday of the month, April through October, from 6:00 to 8:00 p.m., weather permitting. The Town closes the 300 block of High Street, adjacent to Fountain Park, beginning at 5:30 p.m., and owners line up their antique, exotic, classic, or custom cars to share with other auto enthusiasts and the general public. These FREE events are sponsored by Main Street Chestertown and organized by local car collectors Jon and Barbara Slocum, who provide weather updates and more at facebook.com/CarsOnHighStreet.