Main Street Chestertown kicks off another season of free monthly “Cars on High” events on Thursday, April 15, 6-8 p.m., in the 300 block of High Street next to Fountain Park.  Proud car owners will park their antique, exotic, classic, or custom automobiles to share them with other “car people” and the general public. Masks will be required in the display area.

Organized by auto enthusiasts Jon and Barbara Slocum, the event will continue on every third Thursday through October (May 20, June 17, July 15, August 19, September 16, and October 21).  All events will be as weather permits, so check the Cars on High Facebook page ( for updates if the forecast is questionable. 

The 300 block of High Street will be closed starting at 5:30 pm to allow participating cars to get into position.

For questions, email–

Kay MacIntosh
Executive Director, Main Street Historic Chestertown
Manager, Chestertown Arts & Entertainment District
118 N. Cross Street
Chestertown, MD 21620
office: 410-778-2991