First Annual Chestertown Car Show Rolls into Downtown September 14


The first annual Chestertown Car Show will cruise into the heart of the Arts & Entertainment District on Saturday, September 14, from 2:00 to 6:00 p.m., complete with judges’ awards, food and beverages, and auto-related contests and activities. Children can search for car parts in a scavenger hunt, paint hub caps, and compete in a valve-cover car race.

The rain date for the event is Sunday, September 15.

Sponsored by Main Street Chestertown, the show will display cars in and around Fountain Park and along the 300 block of High Street between Cross and Mill streets. All years, makes and models are welcome, and trophies will be awarded in 10 categories:

Vintage Cars or Trucks: 1940 and older.

Modern Domestic Cars: 1976 and newer.

Classic Domestic Cars: 1941 to 1975.

Modern Imported Cars: 1976 and newer.

Classic Imported Cars: 1941 to 1975.

Trucks and Off-Road:  Trucks, Jeeps, sport utility vehicles and any vehicle designed for work or off-road use, of any year and brand.

Pro Street: vehicles of any year and brand that have been modified for drag racing.

Rat Rod: vehicles of any year and brand that exhibit patina or finish and modifications such as lowering, chop tops and other features of the functional hot rods of the 30s, 40s and 50s.

Survivor: Substantially original and unmodified vehicles of any brand, manufactured for model year 1989 and older. Minor paint work and cosmetic or mechanical repairs allowed, but not significant restorations.

Work in Progress:Cars that run and drive but are still projects under construction.

Register online at, where more detailed information about the event and the judging categories is posted.  Day-of registrations will be accepted, as space allows, between 11 a.m. and 1 p.m. in the event headquarters tent at High Street and Spring Avenue. Registration fee is $20 in advance and $25 the day of the show.

The Car Show is being organized by a volunteer committee led by Jon and Barbara Slocum, who also founded Main Street Chestertown’s monthly Cars on High gatherings on the third Thursday of each month from April through October.

The Chestertown Car Show is free to spectators and all are welcome. For more information visit or email

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