Chestertown

A Storied Past

Chestertown dates back to 1706 when it served as a port of entry for colonial settlers arriving to Maryland. It was a prosperous trading and shipbuilding center. In the mid-18th century, Chestertown was one of Maryland's leading ports and was named one of the colony's six Royal Ports of Entry.

Chestertown’s shipbuilding past has been revived through the non-profit Sultana Education Foundation offers Schooner Sultana Project. The Sultana is a replica of a traditional 18th century schooner. It was constructed locally by a non-profit organization, and serves as a floating classroom. Children and adults enjoy hands on educational experiences that focus on history and the study of the natural environment.

Chestertown is also home to Washington College - 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, served as a trustee and received an honorary degree. Washington College is a great resource for Chestertown with access to senior programs and facilities.

Visitors and residents alike are attracted to the area’s natural beauty and its peaceful, small town lifestyle combined with the convenience of being less than two hours from big city amenities. Enjoy the slower pace, walking along the tree-lined brick paths, and popping in to shops and galleries. Some of the local haunts are the Chester River Wine and Cheese Shop, Twigs and Teacups gift shop, Evergrain Bread bakery, Play it Again Sams Coffee Shop and Germaine's Carryout -New Orleans with a twist.

The Chester River Walk leads to waterfront dining at 98 Cannon Riverfront Grille and to The River Packet, a 65-foot classic yacht offering leisurely cruises on the Chester River. The area has many destinations to enjoy boating, hunting, crabbing and fishing, as well as walking and biking in parks and on trails.

Chestertown has a strong community sensibility and is home to many artists and musicians offering live theater and music performances. The Annual Chestertown Tea Party Festival is fun for everyone with folks in period dress, puppet shows, music, local fare and the wacky River Raft Race. The highlight of the weekend is a reenactment of the historic Tea Toss on the Sultana on the Chester River. In the Fall is the Sultana Downrigging Weekend with visiting tall ships offering tours, sailings and a beautiful evening illumination. Other events include the Harry Potter Festival and A Dickens Christmas. Link to information about local activities and events Town of Chestertown.