Need a charming Eastern Shore getaway with colonial history, riverfront views, and small-town charm? Head to Chestertown! Nestled along the Chester River in Kent County, Chestertown is one of Maryland’s best-preserved historic towns. With cobblestone streets, Georgian architecture, and vibrant cultural life, this walkable riverside town blends history, nature, and modern creativity for a delightful escape.
Chestertown, MD Highlights:
- For Adventurous Travelers: Kayak or paddle the Chester River – Rent a kayak or launch from Wilmer Park to explore the peaceful waterways and scenic shorelines.
- For History Buffs: Stroll the Chestertown Historic District – Admire 18th-century brick homes, churches, and the colonial-era Customs House on a self-guided walking tour.
- For Shoppers: Browse High Street boutiques and galleries – Discover antiques, books, art, and gifts in locally owned shops with Chesapeake charm.
- For Couples: Enjoy a wine tasting or romantic stay at a historic inn – Share a sunset drink riverside or relax in a cozy B&B with centuries-old charm.
- For Families: Explore the Sultana Education Foundation or attend a community event – Learn about Chesapeake Bay ecology aboard a replica 1768 schooner or enjoy free concerts in the park.
Best Time to Visit Chestertown, MD
The best time to visit Chestertown is spring through fall (April–October), when the weather is mild and perfect for waterfront walks, festivals, and outdoor dining. Fall brings foliage and harvest markets, while spring offers garden tours and sailing events.
How to Get to Chestertown, MD
- If you are traveling by car: Chestertown is located off MD-213, about 1.5 hours from Baltimore, Philadelphia, or Washington, D.C.
- By Air: The nearest airports are Baltimore/Washington International (BWI) and Philadelphia International (PHL), both within 90 minutes by car.
- By Bus: Limited regional services are available; driving remains the best option for flexibility and exploring nearby small towns.
Where to Stay in Chestertown, MD
- The White Swan Tavern – Historic 18th-century inn offering elegant rooms and full breakfast in a colonial setting.
- Great Oak Manor – Waterfront B&B on the Chesapeake Bay with stunning views, cozy fireplaces, and expansive grounds.
- The Inn at Huntingfield Creek (nearby Rock Hall) – Peaceful countryside retreat with suites and cottages, perfect for couples and nature lovers.
Best Things to Do in Chestertown, MD
1. Admire art at MassoniArt Gallery
Rating: ★★★★★
Start your visit at MassoniArt Gallery, the vision of acclaimed Chesapeake Bay-area gallerist Carla Massoni.
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.
You 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
2. Learn about the cultural history of The Historical Society of Kent County
Stop by The Historical Society of Kent County to learn about the cultural history and legacy of Kent County, Maryland.
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
3. Visit Garfield Center for the Arts at the Prince Theatre
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
Where to Eat:
4. Have dinner at 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
5. Take the kids to 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
For Couples and Singles:
6. Learn about pottery at the Chestertown River Arts
Dedicated to fostering an enthusiasm and love for all things creative, the Chestertown River Arts 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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