10 Stress-Free Chesapeake Bay Towns For A Weekend Retreat
With 11,684 miles of shoreline, the Chesapeake Bay is the largest estuary in the country. Naturally, many towns call this bay home, each reflecting the laid-back lifestyle that comes with being by the coast. If you are in need of some relaxation, you will most certainly find it in these 10 towns, complete with sailing charters, canalside trails, and art museums that will sweep you away from your stress for the weekend.
Cape Charles, Virginia
Situated on Virginia’s east shore, Cape Charles is a Victorian-era planned community with all the seaside spirit you could hope for in a weekend escape. Numerous seafood restaurants are scattered throughout town, with The Shanty being a highlight, serving seaside-to-table dishes since 2012. Cape Charles Natural Area Preserve is the perfect place to get out into nature, protecting an area of forested uplands that visitors can see from an elevated boardwalk, and you can unwind at the end of the day at the Bay Haven Inn, which was built in 1906 as a Colonial Revival home and now welcomes guests in tastefully renovated rooms and suites.
Easton, Maryland
If your idea of a relaxing weekend involves browsing art galleries and museums, you will love visiting Easton. This town has a rich art scene, exemplified by events like the First Friday Gallery Walk, held from April to December, when galleries stay open late and guest speakers often present. Travelers can also spend an afternoon at the Academy Art Museum, which exhibits more than 1,700 works ranging from the 17th century through today. The Hummingbird Inn is a wonderful place to lodge during your weekend. It is located in a restored Queen Anne Victorian home with curated art throughout.
St. Michaels, Maryland
With brick sidewalks, cottages, and white-columned porches, St. Michaels perfectly embodies that postcard image that comes to mind when people think about the Chesapeake Bay. The town’s maritime heritage is also strong, preserved through landmarks like the Chesapeake Bay Maritime Museum, which offers river cruises, tours, and historic exhibitions that dive into the Chesapeake’s culture. Travelers can immerse themselves in this culture first-hand by signing up for a sailing charter. St. Michaels Sailing Charters offers a variety of charters on their catamaran, ranging from two to three hours. To stay near the harbor, consider lodging at St. Michaels Harbour Inn, Marina & Spa, which has a harborfront location, along with an on-site day spa and seasonal outdoor pool.
Onancock, Virginia
Onancock has a wide variety of activities to enjoy in town, but it isn’t so large that it is overwhelming to explore over a weekend. The Onancock Wharf is a hub for water-based recreation, serving as a gateway to boat tours and kayak rentals. When the weather gets cold, pop in for a drink at The Blarney Stone Pub, which also offers plenty of casual fare and live music performances. There are several unique places to lodge during your stay, including The Charlotte Hotel, a luxury boutique downtown that is housed in a 1907 historic building.
Oxford, Maryland
As one of the oldest towns in Maryland, Oxford is brimming with history. There are two prominent museums in town, one of which is the Water's Edge Museum, which tells the story of the country’s Founding Black Families, including farmers, military figures, professional sailmakers, and musicians who paved the way for their descendants. Travelers can also enjoy a ride on the Oxford-Bellevue Ferry, the oldest privately operated ferry service in the US, operating since 1683. To spend the night in one of the town’s historic landmarks, book your stay at the Robert Morris Inn, whose legacy dates back over three centuries.
Irvington, Virginia
While it lies just north of the Chesapeake Bay along Carter's Creek, Irvington perfectly encapsulates the idea of a laid-back waterfront town. Home to just under 500 residents, travelers can spend their weekend strolling through town and stopping into shops and galleries, such as Objects Art and More, which sells jewelry, pottery, sculptures, and paintings representing more than 200 artists. When you start to get hungry, pop into a local restaurant like The Office Bistro and enjoy specials like baby back BBQ ribs, country cob salad, or a hand-tossed pizza on their outdoor deck or cozy indoor seating area. The Hope and Glory Inn is a nice place to call it a night, set on the grounds of a micro-vineyard.
Chesapeake City, Maryland
Located on one of the busiest canals in the world, Chesapeake City is a lively waterfront town filled with well-preserved 19th-century architecture. Travelers can start their weekend with a hike along the Ben Cardin C&D Canal Trail, which connects the canal from end to end, eventually terminating in Delaware City. Afterward, head back into town to browse some of the local shops, like Chesapeake Candy Works, which sells gourmet chocolates, candies, and frozen yogurt. To cap it off and toast a great weekend, grab a beer from Bayheads Brewing Company, which serves craft beers brewed right in Chesapeake City. Travelers also have several adorable inns in town to choose from, such as The Blue Max Inn, a bed and breakfast that was built in 1854.
Rock Hall, Maryland
With a rich heritage of fishing, crabbing, and oystering, it's no secret that Rock Hall is one of the best places in Maryland for seafood. Visitors can start their adventure by learning about the fishing industry at the Waterman's Museum, which has exhibits, photographs, and carvings on display. Once you have the historical context, drop by one of the town’s seafood restaurants for a savory bite, such as Harbor Shack, which serves scallops, crab cakes, seafood pasta, and many other favorites from the sea. For a relaxing evening, book a room at the Osprey Point Inn, a colonial-style residence that also has an on-site restaurant and marina.
Cambridge, Maryland
Founded in 1684, Cambridge is one of the country’s oldest colonial towns, making it another great weekend destination for history lovers. Travelers can visit landmarks like the Choptank River Lighthouse, a replica of the original beacon, or head south to the Harriet Tubman Underground Railroad Visitor Center, which features a film and exhibits about the Harriet Tubman Underground Railroad Scenic Byway's history. Also south of town, you’ll find the Blackwater National Wildlife Refuge, which was formed in 1933 as a sanctuary for migratory birds. The Cambridge House Bed & Breakfast is a classic place in town to spend the night, formerly a sea captain’s manor built in 1847.
Urbanna, Virginia
Although many people know Urbanna for its annual Oyster Festival, it has numerous charming attractions to visit the rest of the year, as well. The Urbanna James Mills Scottish Factor Store is the perfect example, a museum located in an 18th-century store that dives into colonial American history. For a glass of wine or a pint of local craft beer, head over to Urbanna Pearl Oyster Tavern, a beloved watering hole and oyster bar. Visitors will also love staying at The Chesapeake Inn, a boutique hotel with a beautiful garden, luxurious lobby, and 12 uniquely decorated, coastal-style rooms.
Your Relaxing Trip Is Just A Short Drive Away
It is natural to need a break every now and then. Fortunately, those who find themselves near the Chesapeake Bay are just a short drive away from a weekend of rest and relaxation. Visiting wildlife refuges and preserves, browsing local art galleries, and staying in historic inns are just a few of the activities that visitors can enjoy during their weekend away. By the end of your trip, you will most definitely feel refreshed and ready to take on the world once again!
