Registration to exhibit your car is $25 the day of the show. All payments will be by Credit Card or cash.

Scroll down to register for the show!

The Car Show accepts all years, makes & models of cars, trucks in the following judged classes.

Classes and Rules

Registrants should select the class that best suits their vehicle.  Some vehicles may fit into more than one class; it’s the registrant’s choice as to which class they enter.

Vintage Cars or Trucks (1940 and older): All cars domestic or foreign.

Modern Domestic cars – (1976 and newer):  All cars manufactured by a domestic brand (Ford, GM, Chrysler, Tesla, etc…) for model year 1990 and later.  Includes stock and custom cars.

Classic Domestic cars (1941 to 1975):  All cars manufactured by a domestic brand (Ford, GM, Chrysler, Rambler, etc…) from model years 1941 thru 1975. Includes stock and custom cars.

Modern Imported cars – (1976 and newer):  All cars manufactured by a foreign brand (Honda, VW, Jaguar, etc) for model year 1976 and later. Includes stock and custom cars.

Classic Imported cars – (1941 to 1975): All cars manufactured by a foreign brand for model year 1941 to 1975.  Includes stock and custom cars.

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

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 that celebrate the functional hot rods of the 30s, 40s and 50s. 

Survivor:  vehicles manufactured for model year 1989 and older from any brand that are substantially original and unmodified.  Minor paint work and cosmetic or mechanical repairs are allowed but vehicles that have been significantly restored are excluded.

Work In Progress: Cars that run and drive, but are projects under construction.

All Car/Truck classes are judged, with trophies going to BEST in Class!

Special Awards:

  • Mayor’s Trophy
  • Fire Chief’s Trophy
  • Police Chief’s Trophy
  • Arts & Entertainment District Trophy
  • Mechanic’s Trophy
  • Main Street Chestertown Trophy

Chestertown Car Show — Instructions for Attendees on Day of Event

  • Enter the event space at the intersection of High and Cross streets (South end).  No entry is possible from Spring Street, Mill Street, or northern portions of High Street.
  • Provide entry attendant with your registration confirmation email and class. If you have not pre-registered, the entry attendant will tell you where to park.
  • Follow directions to the display section for your class.  Attendants will be available throughout the event space to assist with finding your section.
  • Park in your section, angled back-in parking only, between the white dots on the pavement.  THIS IS VERY IMPORTANT to ensure we have enough space.
  • Check-in at the registration table to get your participant information form.  If you have not pre-registered, payment should be made at the table by credit card or cash.
  • Complete your participant information form and leave it on your windshield if you wish for your car to be judged in the show.
  • All participating vehicle owners are requested to remain for the entire length of the show.
  • Return to your car promptly at the end of show at 6pm.  Chestertown Police may be forced to remove vehicles left on display after the close of the event.
  • All show participants exit the show area at the intersection of Mill and High streets (heading uphill away from the river).