Chestertown is the lovely county seat of Kent County, originally founded in 1706 as one of Maryland's Eastern Shore's earliest settlements and most influential port cities. Today, its gorgeous colonial-era and pioneer-era architecture is preserved in large part on the National Register of Historic Places, including landmarks like the Chestertown Railroad Station, Airy Hill, and the buildings of Washington College. Each year, the city hosts the annual Chestertown Tea Party Festival, which commemorates the 1774 event following the Boston Tea Party earlier that year. Certain attractions may be temporarily closed or require advance reservations. Hours/availability may have changed.

1.MassoniArt Gallery

MassoniArt Gallery
© MassoniArt Gallery

MassoniArt Gallery is the vision of acclaimed Chesapeake Bay-area gallerist Carla Massoni, who has worked with Baltimore and Washington, D.C. architects, design firms, consultants, and nonprofit organizations for more than three decades to bring art into the workplace. The gallery has been honored as part of the prestigious United States State Department's Art in Embassies Program, works to place American artists' work in embassies around the world. Visitors can view the gallery's public art collections and exhibitions Thursdays, Fridays, Saturdays, and Sundays throughout the year and see works by respected artists from around the mid-Atlantic. Past exhibitions have featured artists such as Marc Castelli, Grace Mitchell, and Michael Kahn.

203 High St, Chestertown, MD 21620, Phone: 410-778-7330

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2.The Historical Society of Kent County, Chestertown, MD

The Historical Society of Kent County, Chestertown, MD
© The Historical Society of Kent County

The Historical Society of Kent County is a delightful nonprofit organization that preserves the cultural history and legacy of Kent County, Maryland through the operation of several historic buildings and sites throughout the Chestertown region. The Society provides brochures for self-guided walking tours for area visitors, which explore Chestertown's civic life and culture prior to and during the American Revolutionary War. Visitors can download walking tour maps from the Society's website and learn about buildings with connections to the city's Revolutionary War and colonial-era figures. All tours begin at the Bordley History Center and feature written commentary and information drafted by local historian Robert J.H. Janson-LaPalme.

301 High St, Chestertown, MD 21620, Phone: 410-778-3499

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3.Garfield Center for the Arts at the Prince Theatre

Garfield Center for the Arts at the Prince Theatre
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Garfield Center for the Arts at the Prince Theatre preserves the cultural legacy of Chestertown's historic Prince Theatre, which was originally opened to the public in 1909 as a motion picture house showing silent films. Throughout the 20th century, the theater showed major motion picture releases throughout the week until its closure in August of 1993. Today, the Prince Theatre Foundation has converted the theater into a community theater organization presenting professional-level theatrical and musical productions throughout the year. More than a dozen community theater and arts organizations make use of the space each year, presenting enriching, educational, and entertaining programming for children and adults alike.

210 High St, Chestertown, MD 21620, Phone: 410-810-2060

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4.Emmanuel Chester Parish, Chestertown, Maryland

Emmanuel Chester Parish, Chestertown, Maryland
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Emmanuel Chester Parish is the third church Anglican church of its kind constructed at its site in Chestertown, which originally housed a wooden chapel that was demolished and reconstructed as early as 1720. The present structure's nave was constructed in 1767 and still serves as the entrance to the church today, showcasing impressive design elements throughout its two-story complex. Visitors can explore the church's stunning architectural and design elements, including its beautiful Tiffany stained-glass windows, triptych of Moses and the Ten Commandments, and lovely custom pipe organ. Special events held throughout the year include an annual concert series, which showcases performances by regional classical and faith artists.

101 N Cross St, Chestertown, MD 21620, Phone: 410-778-3477

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5.The Kitchen at the Imperial, Chestertown, Maryland

The Kitchen at the Imperial, Chestertown, Maryland
© The Kitchen at the Imperial

The Kitchen at the Imperial is a lovely dining destination in Chestertown helmed by executive chef and owner Steve Quigg, serving up fine dining options in an unpretentious, comfortable atmosphere. The restaurant offers elegant seating in its main dining room or casual bar space within its charming tavern, which features a full-service bar crafting housemade signature cocktails. Diners can choose from a variety of coastal and continental fare at lunch and dinner, ranging from jumbo lump Maryland crab cakes and pan-seared day boat scallops to pork Wellington, veal piccata, and trout Almandine. Starters like pan-fried oysters, fish charcuterie boards, and Old Bay crab dip can be paired with a top-shelf selection of bourbons, cognacs, and scotches.

208 High St, Chestertown, MD 21620, Phone: 410-778-5000

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6.Procolino's Pizza, Chestertown, Maryland

Procolino's Pizza, Chestertown, Maryland
© Procolino's Pizza

Procolino's Pizza has been a staple on the Chestertown dining scene for more than three decades, owned and operated by Italian immigrants and brothers Vincenzo and Salvatore Scotto. The family-operated restaurant is known for its delicious artisanal pizza offerings, ranging from classic favorites like margherita and spinach bianca pizzas to unique takes like baked ziti pizza topped with penne pasta, ricotta, and parmesan cheese. Diners can also enjoy a selection of other classic Italian menu offerings, including custom-made strombolis and calzones. Delicious appetizer selections include authentic Italian bruschetta, mozzarella Caprese, and antipasto platters.

711 Washington Ave # 9, Chestertown, MD 21620, Phone: 410-778-5900

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7.Figg's Ordinary, Chestertown, Maryland

Figg's Ordinary, Chestertown, Maryland
© Figg's Ordinary

Figg's Ordinary brings the colonial dining tradition of ordinaries into the present day, striving to serve as a community gathering and dining space for Maryland's Eastern Shore. The zero-waste business focuses on eco-friendly practices in all of its operations, encouraging customers to bring their own containers for dining on the go and sourcing all of its wares from local farmers, producers, and diningware makers. Delicious breakfast, lunch, and dinner fare is all free of gluten and refined sugars, great for diners with dietary restrictions looking for a unique dining experience. Diners can choose from favorite dishes like old-fashioned rolled oats, daily quiche specials, artisanal house sandwiches, and protein-packed salads, all of which can be prepared with vegan milk, yogurt, and cheese options upon request.

207 S Cross St #102, Chestertown, MD 21620, Phone: 443-282-0061

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8.Chestertown River Arts

Chestertown River Arts
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Dedicated to fostering an enthusiasm and love for all things creative, the Chestertown River Arts Center is a wonderful community resource. The center offers a wide range of workshops and classes across just about all genres of artistic endeavor, including pottery, sculpting, painting and drawing, textile art and photography. All ages are catered for and KidSPOT encourages children of all ages to participate in many fun and educational arts and crafts. Chestertown River Arts also hosts regular art and cultural discussions and lectures presented by prominent guest speakers. You can check their website to see what’s on during your visit to Chestertown.

Chestertown River Arts, 315 High Street #106, Chestertown, MD 21620, 410 778 6300

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8 Best Things to Do in Chestertown, Maryland

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