The First Annual Chestertown Car Show – 9/14/2019 accepts all years, makes & models of cars, trucks in 10 classes.  There will be over 15 trophies, for specific classes, awarded on a judged basis.

Online Registration is open until 9/13/2019!

The cost per car for pre-registration is $20.00 Register Now

The exhibitor cars will begin parking at 12:30 PM

Day of Show Registration:

Day-of-Show registration (pre-registering is best!) will begin at 11:30 am. Day of Registrations will be at the Car Show table/canopy, which will be located at the Court House Parking Lot on Cross Street. This is across from the Town Hall/Visitors Center.

There is a printable form here: Download Form

Food and Drink:

Beer and Wine will be sold by Mainstreet Chestertown, there will be food and Ice Cream by Lockbriar’s Farm.

There will be restrooms (Port-a-Potties) available on site.

There’s more than just cars and trucks,  in Chestertown, we have a thriving arts district, the Chester River, Sultana and many other things to do. Make plans to come early and stay late, there’s plenty for every family member at the newest car show on the Shore!

Things to See & Do at the Show:

  • Adult Activities
    • Try your luck in the 50/50 Raffle
    • Name – That – Part contest
  • Children’s Activities
    • Hub Cap Painting
    • Valve Cover Racing
    • Face Painting
    • Corn Hole
    • Scavenger Hunt

See our Classes and Rules

Chestertown Car Show accepts all years, makes & models of cars and trucks.