The Chestertown Tea Party festival is a time honored tradition for visitors and residents alike. This weekend long festival has entertainment for all ages. Kick off the Tea Party weekend with the Friday Night Block Party, hosted by Main Street Chestertown. The Block party includes music, food trucks and vendors, beverages, and fun for all […]
The National Music Festival transforms Kent County into a hub of music. The nationally recognized event will feature music to suit virtually every taste — from symphonies and chamber music to hints of jazz. More than 30 concerts and over 200 open rehearsals are scheduled throughout the festival in venues across the Eastern Shore.
The Black Union of Kent County and the Town of Chestertown host the annual Kent County Juneteenth Celebration offering a series of events to celebrate history, culture, and achievements. Fountain Park on Park Row on Friday June 14th (5-7pm) and Saturday, June 15th 12pm-5pm.
Hosted by the Downtown Chestertown Association, Crazy Days is Chestertown’s annual sidewalk sale with businesses offering crazy deals and restaurants offering crazy specials.
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.
