Chestertown Attractions

Chestertown Attractions

Things to Do in Chestertown, MD

The visitor center at the Kent County tourism office at 100 North Cross Street has information on self-guided walking, biking, and driving tours of the county, and a walking guide to the shady, brick streets of the Chestertown Historic District.

Chestertown features many restored 18th century homes, lovely churches, the county courthouse, and several interesting shops.

Grand houses built by wealthy merchants line the Chester River.

Next to the public dock at the bottom of High Street is the old Customs House, built in the 1740’s.

Chestertown’s shipbuilding past has been revived by the recent Schooner Sultana project.  The Sultana, a replica of a traditional 18th century schooner, was constructed locally by a non-profit organization using traditional ship building skills and launched in May of 2001.

The ship serves as a floating classroom offering unique, hands on educational opportunities for children and adults that focus on history and the study of the natural environment.

If you’d like to get out on the Chester River, the Chester River Packet Company offers cruises on their 1920s-style tour boat. They offer a variety of day and night cruises, including luncheon, dinner, and Sunday brunch cruises.

The Schooner Sultana and visiting ships during Downrigging weekend
The Schooner Sultana and visiting ships during Downrigging weekend

To learn about the history of the area, visit the Historical Society of Kent County at the historic Geddes Piper House at 101 Church Alley.  The house contains an impressive collection of 18th and 19th century portraits, furniture, textiles, attire, maps and china.

The display of 18th and 19th century Chinese export tea pots is a major attraction.  There is also a Victorian Children’s Room and changing exhibits which highlight local and Eastern Shore history.

The Geddes-Piper House is open for guided tours Saturday and Sunday, May through October between 1 and 4 pm. During the week when the office is open, visitors can take a self-guided tour.

Chestertown is also home to Washington College.  Washington College is the tenth oldest college in the United States.  The college was founded in 1782 with the help of George Washington who gave his name and 50 guineas to the college.   Washington served as a trustee and received an honorary degree.

Eastern Shore Shorts by Gail Priest. Stories set in Berlin, Cambridge, Chestertown, Chincoteague, Easton, Rock Hall, Salisbury, St. Michaels, and Tilghman island. Buy now at!

For a selection of fresh produce and fine arts and craft, visit the Chestertown Farmer’s Market and Artisan’s Market, located on Park Row in the heart of downtown Chestertown.  You’ll find fresh breads and produce at the farmers market and work by local artists.  Saturdays at 9:00 a.m.  Open from the first Saturday in April to the last Saturday before Christmas.

Located 8 miles east of Chestertown is the Chesapeake Farms Wildlife Habitat.  This 3,000 acre wildlife and agricultural demonstration area has been set aside by the Dupont Company to protect soil, water, wildlife, and waterfowl.

Visitors can drive through the habitat on Wildlife Drive on the north side of MD 20 or on Sanctuary Pond Drive on the south side of MD 20.  You may be able to spot ducks, geese, osprey, and bald eagles.

Where to Stay? Find Chestertown Hotels and Bed & Breakfasts. Make the best choice – all your lodging options, traveler rated and reviewed.