Chestertown Travel Guide

Welcome to Chestertown, MD, Maryland

Located on the banks of the Chester River in Kent County, Maryland, Chestertown sits at the northeast side of a peninsula that juts into the Atlantic Ocean. Yacht clubs, parks and a vast range of outdoor recreational activities are popular in the area. Many animal species coexist because of the unique mix of salt and fresh water, making birdwatching a favorite activity. Hundreds of years of history also create allure for this Maryland town. The unusual architecture of Hynson-Ringgold House (not open to the public) places it among the town's finest historical buildings. Visitors can also discover history by attending the Chestertown Tea Party reenactment that occurs each Memorial Day weekend. Founded in 1782, Washington College, the tenth oldest liberal arts college in the country, is another must-see. Additionally, the annual September fall Candlelight Walking Tour allows the public a peek into the many impressive homes of Chestertown. Today a leisurely walk down the city's cobbled streets unveil old-fashioned ice cream parlors, antique shops, bed and breakfasts, art galleries, fine dining and much more.