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 ages! Saturday’s events start with the 2024 Chestertown Tea Party Run/walk for Radcliffe 5k & 10 miler. After your run/walk, head over to High Street to enjoy the Annual Tea Party parade. Following the parade, walk our historical downtown and enjoy the many food and gift vendors selling one of a kind items. A walking tour of Historic Chestertown is also available. The Tea Party reenactment starts at 2pm and is highlight of the weekend. Finish off your weekend with the Raft Races and tents with food vendors and artisans on Sunday in Wilmer Park.