The Chestertown Car Show – 10/7/2023 (rain date 10/8/2023) accepts all years, makes & models of cars, trucks in 10 classes.  There will be 8 trophies for specific classes, awarded on a judged basis and 4 Special Trophies awarded.

Chestertown, MD 21620

Online Registration is open NOW and closes 10/7/2023!

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

The exhibitor cars will begin parking at 1:15 PM

Day of Show Registration:

Day-of-Show registration is $25, (pre-registering is best!) will begin at 11:00 am.

Day Of ShowRegistrations will be at the Car Show table/tent, which will be located at Memorial Plaza.

Entertainment this year!!!

Music by:

Gravel Road and SoundProof

Food and Drink:

Food Trucks will be onsite

Beer and Wine will be sold by Mainstreet Chestertown.

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!

See our Classes and Rules

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