Chestertown Vacations, Tourism & Travel Information

Chestertown, Maryland is a popular family vacation and romantic getaway destination. Tourism in this historic colonial town on the Chester River centers on a blend of shopping, arts, history, and dining options.

Some kid friendly attractions in Chestertown include the Schooner Sultana, an educational sailing ship built and launched in Chestertown Another great family vacation idea in Chestertown is Durding’s store, and authentic old-time candy store.  Uniquely Chestertown accommodations the family will enjoy are available at the Inn at Mitchell House, which gets rave reviews for its breakfasts. One of the most popular features of a weekend visit the Farmers' Market. You'll find wonderful bread, home- grown produce and even -- occasionally -- puppies and goats.

Looking for things to do in Chestertown for a romantic getaway? There are a dozen or more galleries, studios, and shops featuring the work of local, regional and internationally known artists and craftspeople for your enjoyment. Afterwards, check into the Great Oak Manor Bed and Breakfast or the Widow’s Walk Inn for some authentic accommodations. Chestertown has a large number of annual events and attractions to enjoy as well – and don’t forget about the wide variety of restaurants you can sample on your vacation.