The 10 Can't-Miss Towns on the Chesapeake Bay
Watermen, shipbuilders, and crabbers shaped the small towns along the Chesapeake Bay, and that maritime heritage still runs through the waterfronts of Maryland and Virginia today. In Annapolis, you can tour the US Naval Academy and the Maryland State House, the oldest state capitol in continuous legislative use in the country. On Tangier Island, 12 miles off Virginia’s Eastern Shore, locals and visitors get around by golf cart or bike, and paddlers can follow a water trail that passes through the harbor. Cambridge, known as the hometown of abolitionist Harriet Tubman, is home to the Harriet Tubman Museum and Educational Center. In Onancock, you'll find Ker Place, a restored 1799 Federal-style mansion, along with a variety of downtown art galleries. Read on to discover the 10 can't-miss towns of the Chesapeake Bay.
Chesapeake City, Maryland
Chesapeake City holds the distinction of being the only Maryland town on a working canal, the Chesapeake and Delaware Canal. This Cecil County town is home to fewer than 1,000 people but offers plenty to keep both visitors and locals busy. The C&D Canal Museum, housed in an original 1837 pump house, offers free admission and tells the story of life on the waterway over the years. Pell Gardens Park is a beautiful waterfront park featuring views of the huge cargo ships that traverse the canal, passing under the iconic Chesapeake City Bridge.
If you're looking for gifts handmade by local artisans, check out The Mercantile at Back Creek, on Bohemia Avenue in the historic downtown area. Enjoy lunch, dinner, and/or cocktails and entertainment at the Chesapeake Inn on the water. The best place to stay in downtown is the Inn at the Canal Bed and Breakfast, a Victorian home built in the 1870s that puts visitors in the midst of everything.
Mathews, Virginia
Fewer than 1,000 people live in the tiny, historic, quiet town of Mathews, the county seat of Mathews County on Virginia's Middle Peninsula. With no stoplights, traffic isn't an issue here. While there are no accommodations right in town, Foster's Bethel Beach Inn Bed and Breakfast in Onemo, just five miles from Mathews, is perfect for a comfortable, relaxing getaway.
The Mathews Maritime Museum teaches visitors about colonial shipbuilding and the culture of the town's founding watermen. Bay School Community Arts Center in Mathews will appeal to art lovers and those who want to buy or try art themselves. Richardson's Cafe serves lunch and dinner, as well as wines and craft beer, at the corner of Church and Main Street. Don't miss the Mathews Farmers Market, held on Saturdays from April through October, where you can purchase produce from local farmers and arts and crafts from local artisans.
Annapolis, Maryland
Although it is the capital of Maryland, with just over 40,000 residents, the maritime town of Annapolis is not the huge, bustling city you might expect. This town blends 18th-century colonial heritage with a waterfront lifestyle on the Chesapeake Bay. You have your pick of attractions, from the historic Maryland State House, the oldest state capitol in continuous legislative use in the country, to the US Naval Academy, which is open to the public for self-guided and guided tours.
Annapolis' City Dock is the town's lively waterfront district, featuring restaurants like Iron Rooster. Irish Traditions on Main Street offers Celtic jewelry, fashion, and more. Book your lodging at Annapolis Waterfront Hotel, the only hotel directly on the water in town. In addition to a variety of room types, the hotel includes a fitness center, business center, and boat slips.
Tangier Island, Virginia
Located 12 miles off the eastern shore of Virginia, the small, one-mile-wide by three-mile-long Tangier Island in the Chesapeake Bay is home to fewer than 500 people. It provides a glimpse into a world that is far from the mainland maritime mainstream. Tangier Island is accessible only by boat or small plane, and there are few cars on the island. You can rent golf carts or bikes, or walk, to get around and see everything there is to see. The Tangier History Museum explores the island's heritage, from the War of 1812 to its working watermen. Explore the Fort Albion Site, where the British built a military base during the War of 1812.
The Brigadune Inn bed and breakfast is a top pick for visitors, offering rooms with private bathrooms and awesome bay views. Tangier Island Beach is an unspoiled, quiet stretch of beach with open shoreline access that must be seen to truly be experienced. Don't miss the many Water Trails that you can kayak, including the Orange Trail, passing through the harbor and under bridges.
Crisfield, Maryland
Go almost as far south as you can in Maryland, and you'll come to the small town of Crisfield, home to under 3,000 full-time residents, in Somerset County on Tangier Sound. You can sample some of the town's famous crabs, as Crisfield is known as the Crab Capital of the World, at The Crab Place on Maryland Avenue. Visitors can also go crabbing off Somers Cove Marina during the recreational blue crab season, from April through mid-December. Janes Island State Park on the Annemessex River is the best place to bunk for the night in Crisfield, either in one of its cabins or many campsites. It also contains 30 miles of water trails where you may spot wildlife such as eagles, ospreys, diamondback terrapins, and river otters.
Onancock, Virginia
Captain John Smith called Onancock, Virginia, the "gem of the Eastern Shore" in the 1600s. This can't-miss town, sitting on the Onancock Creek (which flows into the Chesapeake Bay), is still a gem today. Just 12 miles east of Tangier Island, it is another waterfront town where history and art combine. Check out Ker Place, a restored 1799 Federal-style mansion that serves as the headquarters of Shore History, a living history museum. The Onancock Wharf and Marina is a public marina with dock-and-dine options, such as the Charlotte Hotel and Restaurant, which also offers comfortable accommodations. A variety of downtown art galleries, such as Crockett Gallery, will please the art-loving traveler. North Street Market is a specialty gourmet market and cafe that appeals to both locals and tourists.
Cambridge, Maryland
At first glance, the small Dorchester County town of Cambridge, on the Choptank River, an estuary of the Chesapeake Bay, appears to be just another beautiful maritime town. However, it is also the hometown of abolitionist Harriet Tubman. A visit to the town's Harriet Tubman Museum and Educational Center and, just south of town, the Harriet Tubman Underground Railroad National Historical Park is a must for visitors to better understand the importance of Cambridge in our nation's history.
Cambridge is also famous for the Choptank River Lighthouse, a replica of an earlier lighthouse that is available for touring from May through October. Blackwater National Wildlife Refuge, encompassing 28,000 acres of tidal marshlands and home to bald eagles, osprey, and other waterfowl, is an ideal place to relax and appreciate the natural beauty surrounding you. When you have finished touring Cambridge, check into the Cambridge House Bed and Breakfast, located in the town's historic, walkable downtown area, for a comfortable place to sleep and to grab a bite to eat the next morning.
Kilmarnock, Virginia
Kilmarnock, on the lower Northern Neck peninsula of Virginia, is a historic small town with lively dining and shopping options as well as waterfront access to the Chesapeake Bay and Rappahannock River. The Kilmarnock Inn Bed and Breakfast, with eight Presidential-themed cottages, is the perfect place to stay to be in the middle of the action downtown. Guests can eat at Filibuster's Restaurant on-site.
Kilmarnock Town Centre Park consists of nine acres in the middle of town with a playground, splash pad, open-air gym, and amphitheater where live music concerts are held in the summertime. Lee's Restaurant, a fourth-generation locally owned establishment, serves homemade pies and regional country-style food. Main Street shops like The Rivah and Cathy's Unique Pursuits are individually owned local boutiques that help define Kilmarnock's small-town character.
Oxford, Maryland
The coastal village of Oxford, Maryland, on the Tred Avon River, which flows into the Chesapeake Bay, is one of Maryland's oldest towns, founded in 1683. Today, Oxford is home to under 1,000 residents and is a prime example of a relaxed, historic, must-see town. Be sure to ride the Oxford-Bellevue Ferry during your visit. Operating since 1683, this is the oldest continuously running privately operated ferry service in the U.S.
The Oxford Museum, on Morris Street, showcases artifacts on the rich history and continuing role of the town in the water-oriented region. Oxford Town Park provides panoramic views of the bay and its colorful sailboats. Sandaway Suites & Beach is a boutique hotel with its own private beach, well-suited for both families and couples.
Cape Charles, Virginia
If you cross the mouth of the Chesapeake Bay from Virginia Beach into Northampton County, you'll come to the smaller, quieter town of Cape Charles, Virginia. This village beach town attracts visitors, but not the quantity found in the larger resort town across the bay. It also has the only free public beach on Virginia's Eastern Shore, Cape Charles Town Beach. This family-friendly beach is a nice change from the busier beaches across the bay.
Residents and visitors favor golf carts to get around the compact, grid-layout of this historic town, which was founded in 1884 as the southern terminus of the New York, Philadelphia and Norfolk Railroad. The Hotel Cape Charles, right in the heart of the town's historic district downtown, is the perfect central hub for your visit. Craft beer lovers should check out Cape Charles Brewing Company, which serves its own IPAs as well as pub-style fare. Nature will surround you when you visit the Eastern Shore of Virginia National Wildlife Refuge, consisting of 1,127 acres of maritime forests, grasslands, salt marshes, and beaches. Here, you might see falcons, hawks, bald eagles, and a variety of foxes and deer.
Beguiling Bay Towns
The Chesapeake Bay is the largest estuary in the US, covering 4,480 square miles of surface area. Within its region, these inviting towns in Virginia and Maryland are great for a getaway of any length, and for visitors of all ages. Whether you prefer a historic maritime town like Annapolis, bustling with people and landmarks, or a waterfront town such as Oxford, which carries its own rich history on a smaller scale, visiting any of these 10 can't-miss Chesapeake Bay towns will satisfy your desire for a peaceful holiday.
