9 Off-The-Beaten-Path Towns on the Chesapeake Bay
The Chesapeake Bay is the largest estuary in the United States and borders six states. It has a long maritime history, and the villages and towns along its banks honor this past through their preserved buildings and traditions. These nine off-the-beaten-path places are among the best to visit in the bay for their lack of crowds, tranquil surroundings, and exciting areas to explore.
Another interesting aspect of these coastal villages is their abundance of historical architecture that has been carefully preserved. Some are museums, while others now house modern amenities, such as shops or restaurants. This blend of old and new is a fitting way to meld the past with the present, carrying their unique heritage forward for future generations to appreciate.
Onancock, Virginia
Onancock, Virginia, is perfect for kayakers to enjoy the tranquil coastal surroundings and for art enthusiasts. The small town boasts an unparalleled artistic vibe, on display at showrooms like the Danny Doughty Gallery and the Red Queen Gallery. The compact downtown area is also famous for its museums and world-class dining options.
Ker Place, built between 1799 and 1803, is considered the finest example of Federalist architecture on the Eastern Shore of Virginia. It is also a Virginia Historical Landmark that interprets regional history through exhibits, an archaeology lab, and a library. After a day spent discovering Onancock, stop for dinner at one of the many restaurants, such as Mallards at the Wharf or Market Street Grill.
Irvington, Virginia
Irvington is a small coastal village situated on the Rappahannock River, renowned for its natural surroundings and bird-watching opportunities along the river. It also celebrates Virginia's tidewater heritage through cultural exhibits, such as the Steamboat Era Museum. The museum interprets the pivotal maritime trade of the region through exhibits and docent-led tours. While in town, don't miss Objects, Art, and More, featuring a broad collection of art from over 200 artists across various mediums.
Dinner never disappoints at the elegant The Dog and Oyster Micro Vineyard. It is situated in the middle of the landmark The Hope & Glory Inn and specializes in pairing delicate wines with famous Rappahannock River oysters for a memorable feast. Irvington seamlessly blends important history with sophisticated surroundings, making it one of the best villages to visit on the coast.
North Beach, Maryland
North Beach is a family-friendly beach town with quaint amenities and cultural attractions, including museums honoring its regional history. The Bayside History Museum is a must-visit stop while in town. Its exhibits tell the cultural and natural history of North Beach and the Chesapeake Bay, including paleontological exhibits and items from the War of 1812.
Today, the town revolves around the pier, with all shops and venues within walking distance. Wetlands Overlook Park, located on the north end, and the new Mark R. Frazer Sunrise Garden offer peaceful respites and an excellent opportunity to bask in the salt-tinged air. The vibrant community hosts movies on the beach in the summer and annual events, such as the Wine, Spirits, and Craft Beer Festival, making it one of the best times to visit this throwback beach town.
Cambridge, Maryland
Historic Cambridge was founded in 1684, making it one of the oldest settlements in the United States. Many of the nation's histories are woven into the fabric of the community, particularly those surrounding the Underground Railroad. Harriet Tubman made her first public act of defiance here at the Bucktown General Store when she was a young girl, and it is available to the public today.
Visitors can also explore the roots of this cause at the Harriet Tubman Underground Railroad Visitor Center and follow the Underground Railroad Scenic Byway. Of course, maritime history also has a significant presence. Visitors are encouraged to visit the Federalist-style Richardson Maritime Museum for a deeper historical dive. You can also book a cruise aboard the Nathan of Dorchester to view this extraordinary town through a maritime lens.
St. Michaels, Maryland
St. Michael's is a beautiful waterfront town on the Eastern Shore. It is hard to pick just one distinctive feature, but the harbor is the heart of the hamlet, with stunning views that are best enjoyed aboard the Selina ll sailing ship. You can learn more about its history at the Chesapeake Bay Maritime Museum. Afterward, take a walk down Talbot Street for the best dining and shopping options around.
The de facto Main Street features unique finds, such as the Book Hound, a popular bookstore housed in a 1920s Victorian house with a bright pink door. After grabbing your favorite yarn, stop at the Lyon Rum and Windon Distillery in historic Old Mill for an aperitif or cocktail. They offer free samples daily and are located across the street from the Classic Motor Museum, another fun stop in this historic town.
Betterton, Maryland
Betterton started as a small fishing village along the Sassafras River and has a population of under 1,000 residents. People come here to enjoy tranquil Betterton Beach, a five-acre family-friendly shoreline. Another peaceful waterfront escape nearby is Rock Hall, known for its marinas, fresh seafood, and over 700 feet of scenic shoreline. This is the place to be if you are seeking a quiet and relaxing beach with few crowds and lovely views.
After soaking up the rays, grab a bite to eat before you head out of town. Local favorites include Sassafras and Marzella's by the Bay. Sassafras is a cottage restaurant serving traditional Chesapeake seafood and offers reservations for its Chef's Counter, where the chef serves guests. Marzella's serves lighter fare, such as burgers and pizzas, and is a popular lunch spot. Betterton is definitely off the beaten path for most, which only adds to its allure for many.
Chesapeake City, Maryland
Visiting historic Chesapeake City feels like going back in time. Originally named Bohemia Manor, the name change took place during the construction of the Chesapeake and Delaware Canal in 1829. This history, along with others, can be explored at the Chesapeake City Museum through exhibits and artifacts. The museum also interprets the vibrant Ukrainian community that settled in this area in the early 20th century.
Other interesting attractions include the old-timey Chesapeake Candy Works for retro candies and other goodies. After getting your fill, relax at the charming Pell Gardens, a waterfront park with brick pillars and an archway, for spectacular harbor views. Hikers will enjoy the Ben Cardin C&D Canal Trail, a 17-mile segment of Delaware's Mike Castle Trail, another fascinating element of this city.
Havre de Grace, Maryland
Historic Havre de Grace is one of the prettiest small cities on the Chesapeake Bay. It features several fascinating museums, including the Concord Point Lighthouse, the Keeper's House Museum, and the Havre de Grace Maritime Museum. Both highlight the immense history behind this town and its development throughout the centuries. This is an elegant town to explore on foot, offering many impressive sites to discover.
Main Street is another reason to visit. The district is filled with cultural delights, such as Anita's Treasures, which specializes in curated goods, and Bahoukas Antique Mall & Beer MuZeum, featuring antiques and beer memorabilia. Dining is an art form in town at spectacular places like MacGregor's and wineries such as Mount Felix Vineyard & Winery.
Solomons Island, Maryland
Solomons Island is a classically maritime village known for its stunning views of the Patuxent River from its Boardwalk. Another favorite landmark is nearby, Drum Point Lighthouse. The lighthouse is a preserved screw-pile lighthouse at the Calvert Marine Museum and is open to the public. Visiting both the museum and the lighthouse provides a glimpse into the importance of this island for its residents and the ships plying the waters.
Booking a room at the Solomon's Inn Resort and Marina will put you near most of the attractions. The modernly stylish resort offers several convenient amenities and stunning views of the Patuxent River, making for an unforgettable stay. The island is unique in that it has carefully preserved its historical sites, complemented by sophisticated lodging and dining options, offering a distinctive way to experience a classic Chesapeake Bay village.
Chesapeake Bay towns are vibrant coastal communities rich in history and intrigue. The off-the-beaten-path villages that dot the landscape offer a chance to escape the crowds while still experiencing the region's rich heritage. The small communities depend on this unique waterway for many reasons, and seeing this connection between the two is awe-inspiring.
The restaurants and shops in the entertainment and historic districts reflect the rich maritime heritage of this area. Visiting historic homes like Ker Place feels like walking into a different time and is often a highlight of any visit. The landmark architecture provides a tangible clue to what made these cities thrive economically, as well as the efforts the community puts forth to save them for future generations. Next time you travel through the Mid-Atlantic region, stop at any of these destinations for an unforgettable experience.
