Signature Event

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 Sultana Education Foundation's Downrigging Weekend highlights Tall Ships and Bluegrass, along with nautical history and Chesapeake Bay ecology.

Kick off the Holiday Season with one of Downtown Chestertowns most iconic events, the arrival of Santa and Mrs. Clause on a fire truck! Enjoy the festive holiday music, candy, and some of the most iconic characters of the holiday season enjoying the downtown.