Chestertown, Maryland, United States Guide
Chestertown offers a delightful escape to Maryland's historic Eastern Shore, a place where the echoes of colonial history resonate along the tranquil Chester River. As you wander its charming, tree-lined streets, you'll discover beautifully preserved 18th-century architecture and a palpable sense of heritage, particularly down by the waterfront. This isn't just a town stuck in the past; it's a vibrant blend of old and new, invigorated by the presence of Washington College, which lends a youthful energy and a surprisingly robust cultural scene, complete with art galleries and performance spaces. For those drawn to the outdoors, the river beckons for kayaking or paddleboarding, while nearby natural areas provide excellent opportunities for birdwatching and gentle exploration. However, it's worth noting that Chestertown operates on a decidedly relaxed pace. If your idea of a perfect evening involves a bustling nightlife or an extensive array of late-night dining options, you might find things winding down earlier here than in larger cities. Also, to truly explore the charming historic district comfortably, or to venture out to the surrounding natural beauty and attractions, having your own vehicle is almost a necessity, as public transportation options are extremely limited. Come prepared for a quiet, scenic retreat rather than a fast-paced urban adventure, and you'll find plenty to appreciate in this charming river town.
Food & Cuisine
Chestertown offers a diverse culinary scene, with a focus on fresh seafood and locally sourced ingredients. Many restaurants feature Chesapeake Bay specialties like crab cakes, oysters, and rockfish. For a casual bite, try one of the waterfront restaurants with outdoor seating. For a more upscale dining experience, several establishments offer refined menus with creative dishes. The Saturday morning Chestertown Farmers' Market is a great place to sample local produce, baked goods, and artisanal products. Popular restaurants include The Kitchen at the Imperial Hotel, known for its elegant ambiance and seasonal menu, and Evergrain Bread Company, a local favorite for artisan breads and pastries.
Nightlife
Chestertown's nightlife is generally relaxed and revolves around its restaurants and bars. Several establishments offer live music on weekends, particularly in the downtown area. The Imperial Hotel's bar is a popular spot for cocktails and conversation. For a more casual atmosphere, consider visiting one of the local pubs. While not a bustling metropolis, Chestertown offers a pleasant and convivial atmosphere for an evening out.
Best Time to Visit
The best time to visit Chestertown is during the spring (April-May) or fall (September-October). The weather is mild and pleasant, perfect for exploring the town and enjoying outdoor activities. Spring brings blooming flowers and vibrant greenery, while fall offers stunning foliage along the Chester River. Summer can be hot and humid, while winter can be cold and occasionally snowy.
Transportation
Public transportation options within Chestertown are limited. The town is easily walkable, especially the historic downtown area. For getting around the wider Kent County area, personal vehicles are generally necessary. Some taxi services and ride-sharing options may be available, but their availability can be limited, especially outside of peak season.
Airport
The closest major airport to Chestertown is Baltimore/Washington International Thurgood Marshall Airport (BWI), which is approximately 70 miles away. From BWI, you can rent a car and drive to Chestertown, which takes about 1.5 to 2 hours depending on traffic. There are no direct public transportation options from BWI to Chestertown.
Attractions
Whitehall Tavern
Dine at this historic tavern, known for its traditional American cuisine and cozy atmosphere. Experience a taste of local flavors and enjoy a meal in a charming setting. It's a great place to relax and savor the culinary delights of Chestertown.
Washington College
Visit this historic liberal arts college, founded in 1782 with the support of George Washington. Explore the beautiful campus, attend a performance, or learn about its rich history. It's a great place to experience academic life and admire the architecture.
Wilmer Park
Enjoy a relaxing day at Wilmer Park, offering green spaces, picnic areas, and views of the Chester River. It's a great spot for a leisurely stroll, a picnic lunch, or simply enjoying the outdoors. A perfect place for families.
Chestertown Tea Party Festival
Attend the annual Chestertown Tea Party Festival, a reenactment of the town's own tea party protest against British rule. Enjoy historical demonstrations, crafts, food, and entertainment. It's a fun and educational event for all ages.
Historic Chestertown Waterfront
Stroll along the Chester River, enjoying the scenic views and historic architecture. Watch boats, dine at waterfront restaurants, and experience the charm of this colonial port town. It's a great place for a relaxing walk and soaking in the atmosphere.
Sultana Education Foundation
Learn about the Chesapeake Bay's history and ecology through educational programs and exhibits. Take a sailing trip on the Sultana, a replica of an 18th-century schooner. It's an engaging and informative experience for all ages.
Brampton Inn
Stay at this charming bed and breakfast, offering comfortable accommodations and a relaxing atmosphere. Enjoy a delicious breakfast and explore the historic town of Chestertown. It's a perfect getaway for couples and those seeking a peaceful retreat.
MassoniArt Gallery
Explore contemporary art at this gallery, showcasing a variety of mediums and styles. Discover new artists and find unique pieces to add to your collection. It's a great place for art lovers to browse and appreciate creativity.
The Garfield Center for the Arts at the Prince Theatre
Enjoy live performances, including theater, music, and dance, at this beautifully restored historic theater. Check the schedule for upcoming events and experience the vibrant arts scene in Chestertown. It's a cultural hub for the community.
Day Trips
Washington, D.C., the nation's capital, is a city brimming with iconic monuments, world-class museums, and historical landmarks. Visit the White House, the Capitol Building, and the Lincoln Memorial. Explore the Smithsonian museums, including the National Air and Space Museum and the National Museum of Natural History. Washington, D.C. offers a captivating blend of history, culture, and political significance.
Approximately 2 hours 30 minutes by car Annapolis, the capital of Maryland, offers a charming blend of maritime history and colonial architecture. Explore the United States Naval Academy, wander along the historic City Dock, and indulge in fresh seafood at waterfront restaurants. The city's vibrant arts scene and numerous boutiques add to its appeal, making it a perfect day trip for history buffs and those seeking a picturesque escape.
Approximately 1 hour 15 minutes by car Baltimore, a vibrant city with a rich industrial past, offers a diverse range of attractions. Explore the Inner Harbor, home to the National Aquarium and historic ships. Delve into art at the Baltimore Museum of Art or the American Visionary Art Museum. Catch an Orioles game at Camden Yards or explore the historic neighborhoods of Fells Point and Little Italy. Baltimore provides a dynamic urban experience with something for everyone.
Approximately 1 hour 30 minutes by car Philadelphia, the birthplace of the United States, is a city steeped in history and culture. Visit Independence Hall and the Liberty Bell, explore the historic Old City, and climb the "Rocky Steps" at the Philadelphia Museum of Art. Indulge in a Philly cheesesteak and explore the vibrant Reading Terminal Market. Philadelphia offers a captivating blend of historical landmarks, world-class museums, and diverse culinary experiences.
Approximately 2 hours by car Cape May, a charming Victorian seaside resort, offers a relaxing escape with beautiful beaches and historic architecture. Stroll along the promenade, explore the historic district filled with Victorian homes, and enjoy the ocean views. Visit the Cape May Lighthouse, go birdwatching at the Cape May Bird Observatory, or take a dolphin-watching tour. Cape May provides a delightful blend of relaxation and historical charm.
Approximately 2 hours 30 minutes by car Washington, D.C.
Travel Time
Activities
Annapolis
Travel Time
Activities
Baltimore
Travel Time
Activities
Philadelphia
Travel Time
Activities
Cape May
Travel Time
Activities