Things to Do
Movies, live music, and art galleries. Outdoor activities. Shopping! Chestertown offers plenty of attractions for students looking for a little R&R.
Arts and Theater
The Prince Theatre at the newly-renovated Garfield Center for the Arts is the premiere spot for drama lovers in town. In addition to the plays (which often feature students in leading roles), the center sponsors jazz festivals, open mic nights, and other student-friendly events.
Movie lovers, don’t fret—Chestertown has its very own movie theater. While it’s not the stadium-seating multiplex you may be used to, you can still catch the biggest blockbusters here. Nearly the entire student body comes out to midnight releases, making the Chester Five feel like the capital of Goose Nation.
Chestertown is home to many art galleries where you can appreciate the talent of local artists, talk to them about their craft, and purchase their beautiful creations. Chestertown River Arts also sponsors an annual studio tour where more than 50 local arists open their studios to visitors, offering refreshments and conversation. These self-guided tours are free, and provide the opportunity to see artists in their working environments.
On the first Friday evening of every month, Chestertown is bustling. Stores extend their hours and open their doors to visitors, providing food and entertainment. You’ll recognize lots of faculty and staff among the throngs of people enjoying live music, free samples, and the genial atmosphere.
On Saturday mornings from April through December, Fountain Park is home to the Chestertown Farmers Market. You can stroll through the stalls and buy vegetables, breads, soaps, and assorted homemade crafts.
Chestertown holds several festivals throughout the year. Downrigging Weekend takes place in late October when tall ships come to Chestertown. See the ships illuminated by lights and fireworks, and take a tour of some amazing historic vessels.
There’s also the Chestertown Book Festival and Locavore Lit Festival, which celebrate the literary heritage of the Eastern Shore and invite well-known authors to our town.
Taste of the Town is a must-attend event that seems to be under the radar. For a small fee, you can buy tickets that you can exchange for samples of food from local restaurants, who set up shop in Fountain Park for the day.
The Chestertown Tea Party celebrates a colonial protest. Legend has it that on May 23, 1774, Chestertown revolutionaries boarded the brigantine Geddes, and threw her cargo tea into the Chester River. Now the event is celebrated with vendors, family activities, a re-enactment, and more. The multi-day event takes place through Memorial Day weekend.
And, if you take a trip back to C-town during the summer, be sure to check out the National Music Festival in June. Bringing together established and apprentice musicians, the festival features more than 200 concerts, events, and rehearsals open to the public.
New to Chestertown is the Chestertown Harry Potter Festival. Held in October, the festival celebrates the famous wizard as well as promotes local businesses and arts.
Flyers posted around town will tell you about other interesting festivals, like the Jazz Festival in September and Wildlife Festival in November. So take a stroll through Chestertown one day and see what hidden gems you discover.
The Great Outdoors
From April through December, check out the Sultana Center on Cross Street. They have a variety of educational exhibits of interest to anyone who loves history or the Chesapeake region. Be sure to check out the small aquaria they have on display, featuring locally-caught fish and turtles. You can purchase some Sultana swag as well. You can see about taking a trip on the Schooner Sultana as well.
Rails to Trails
Opened in the summer of 2012, the Rails to Trails walking and biking trail is already pleasing locals and students. Why not take the scenic route during your your daily run?