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The Unexpectedly Artsy Charm of Chestertown, Maryland

Chestertown immediately impresses visitors with its vibrant arts and live performance scene. At the heart of this is River Arts Chestertown, offering hands-on classes, workshops, and skill-building sessions for teens and adults. The organization also supports educators and artists with ongoing professional development. Visitors can explore a gallery featuring new exhibits on the first Friday of each month, visit the Clay Studio, or browse their shop for unique creations by local artists. Not to be missed is the Garfield Center for the Arts at the Prince Theatre, which features live performances of popular plays and offers a summer camp for children. It also hosts a jazz festival, where music fills the air and residents and visitors share in a celebration of live music. Perhaps the town’s most celebrated event is the Chestertown Tea Party Festival, commemorating the Boston Tea Party, where costumed performers board the authentic reproduction schooner SULTANA as part of the lively waterfront reenactment.

The schooner SULTANA is a replica of the smallest schooner ever commissioned by the British Royal Navy and is a highlight on Chestertown’s waterfront. Sultana’s Mission: “Provide transformative educational experiences in which students investigate the natural and human history of the Chesapeake Bay while exploring solutions for a more sustainable ecosystem.”  In support of this mission, it educates more than 4,500 students annually. Every Friday from 10:00 to 11:30 a.m., there are activities for toddlers. Starting in May, families with children over five can join two-hour sailing trips and help the crew raise the sails. Visitors can tour the crew’s quarters or take a two-hour cruise on the Chester River to enjoy the scenery and watch for waterfowl. The Chester River Yacht and Country Club also offers traditional sailing lessons.

Even with an emphasis on the arts and the waterfront, there are still a lot of traditional small-town activities to enjoy.  Your sweet tooth can be satisfied at multiple places that offer homemade ice cream and pastries. You can even enjoy upscale dining at The Kitchen at the Imperial. Steve Quigg, who leads the kitchen, has been recognized as the “Best Chef on the Eastern Shore” for multiple years.  Of course, there are local shops all along High Street. If you are looking to stay overnight, consider Brampton 1860, an adults-only Bed and Breakfast. For a taste of 18th-century charm, the White Swan Tavern—a pre-Revolutionary landmark—offers a beautifully restored and elegant stay in historic Chestertown. While not open to the public, Widehall, located at the end of High Street, is an architectural gem built by Thomas Smyth III (1730–1819), a judge and key figure in Maryland colonial history. Finally, no trip to Chestertown should be considered complete without a visit to Washington College, one of the oldest colleges in the country, founded in 1782.