Things To Do
About Chestertown
Chestertown is a National Historic Landmark on the Eastern Shore of Maryland. The town was initially one of Maryland's key shipping ports and has a large collection of 18th and 19th century architecture. The quaint town is located on the Chester River and offers various things to do.
Downtown Celebrations
First Fridays of every month comes with a downtown celebration from 5-8 pm. This is a free event sponsored by Chestertown's downtown merchants, community organizations, and art galleries. Lots of food, fun and drink specials. Galleries stage openings and special events. Don’t forget the Welcome Party starts at 7:00 pm at Brittland Manor.
Farmer's & Artisan Market
Saturday morning 8-12 in downtown Chestertown, High & Cross Street.
Water Activities
Public Paddles-kayaks and paddle boards ~2.5-hour tours. Public Sails – ~ two-hour sail on a replica schooner. River Packet Cruises ~ 1.5 hours cruises aboard a 65-foot yacht along the Chester River.