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Chestertown Car Show Rolls into Downtown October 2

September 2, 2021 by James Dissette

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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.

The rain date for the event is Sunday, October 3.

Sponsored by Main Street Chestertown, the show will display cars in and around Fountain Park and along the 200 & 300 blocks of High Street. 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 the model year 1989 and older. Minor paintwork 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 ChestertownCarShow.com 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 Memorial Park. 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 September.

The Chestertown Car Show is free to spectators and all are welcome. For more information visit ChestertownCarShow.com or email [email protected].

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

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Letters to Editor

  1. Stephan Klingelhofer says

    September 3, 2021 at 4:09 PM

    Why is this auto show sitting on the Fountain Park, fragile as it is? Cars should be on the streets, not on urban parkland, compressing the earth and damaging trees, plants, and grass.

    The town which has invested so much and the volunteers who work so hard to maintain the park as a beautiful, restful place for pedestrians, visitors, and townspeople, should not have to repair the damage caused by this event. Or perhaps the organizers should pay?

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