The Chestertown Car Show accepts all years, makes & models of cars, trucks in 10 classes. There will be over 10 trophies for specific classes, awarded on a judged basis. Food Trucks will be onsite. Beer and Wine will be sold by Mainstreet Chestertown. 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!