7 Underrated Towns in Chesapeake Bay

The Chesapeake Bay area is beloved by locals and tourists alike for its natural beauty and allure. Chesapeake Bay loosely translates to “mother of waters” or “great shellfish bay.” Both are suitable nicknames as the entire Bay area is known as a hub for tasty seafood and water-based activities. It is this reputation that makes the Chesapeake Bay area a perfect summer trip destination. Between tiki cruises on Solomon’s Island and the private sandy beaches in Oxford, Maryland, there’s always a little fun under the sun to be had here. 

Oxford, Maryland

Known as one of the oldest towns in Maryland, Oxford boasts beautiful scenery and a rich historic background. Visitors will find a mix of museums, well-kept outdoor areas, and plenty of water-based activities to enjoy here. Those planning on spending a night or two in town will want to book accommodations at Sandaway Suites & Beach. The hotel is located in Oxford’s historic district and offers access to a private sandy beach where guests can swim and enjoy the quiet.

For more fun on the water, try booking a ride on the Oxford Ferry. The ferry has been in operation since 1683 and takes passengers across the sparkling Tred Avon River to nearby Bellevue, Maryland. After spending some time traipsing through Bellevue, board the ferry again to head back to Oxford where museums like the Water’s Edge Museum and The Oxford Museum are waiting to be explored.

Cape Charles, Virginia

Cape Charles, Virginia is a small paradise for outdoor lovers. Spend some time swimming in the Chesapeake Bay at Cape Charles Beach. Here, beachgoers can explore the fishing pier, dig their toes in the sand, and admire the bay views. Just 10 miles from the beach, travelers with cars will find the scenic Chesapeake Bay-Bridge Tunnel. The bridge stretches 17.6 miles long and features plenty of places to stop off and soak up the surrounding views.

After that, head back into town and check out the Cape Charles Natural Area Preserve where hiking and bird watching are on offer. Those hoping to get more glimpses of local wildlife can also visit the Eastern Shore of Virginia National Wildlife Refuge. The refuge also offers hiking trails and fishing opportunities. 

Chesapeake City, Maryland

Chesapeake City, Maryland is a beautiful small town with plenty to offer visitors. Start your visit by exploring Pell Gardens Park. The park is a favored spot for photos as it offers picturesque views of the water and the nearby Chesapeake City Bridge. In the summer, it’s not uncommon to stumble upon free concerts and events in the park as well.

Next, dig into the history of the town and its canal at the C&D Canal Museum. After getting your fill of canal history, hop in the car and take a quick 5-mile drive across the Maryland/Delaware border to Lums Pond State Park. Here, visitors can enjoy a wide range of activities including hiking, zip lining, camping, paddling, and more.

Williamsburg, Virginia

If scenic drives and nature preserves aren’t quite your speed, then the activities in Williamsburg, Virginia will surely appeal. Upon arrival head to Busch Gardens Williamsburg, a local amusement park featuring roller coasters, rides, animals, and live shows. Then cool down with a visit to the park’s sister location, Water Country USA. Here, enjoy water slides, a lazy river, pools, and splash pads. Then top it all off with a round of family-friendly golf at Pirate's Cove Adventure Golf. Of course, Williamsburg isn’t all waterslides and rollercoasters, the town boasts plenty of laid-back activities as well. Travelers can easily find various themed walking tours including a pirate-themed walk through Colonial Williamsburg. 

Yorktown, Virginia

Just under 15 miles from the thrills of Williamsburg, travelers will find an equally appealing place called Yorktown, Virginia. An ideal spot for history buffs, the town is home to several museums and is known as the place where Lord Cornwallis surrendered. This surrender is said to have essentially ended the American Revolution. Today, visitors can learn about this event and several others at places like the Yorktown Battlefield, The Watermen’s Museum, and The American Revolution Museum.

Also located in the historic district is Yorktown Beach. Here, travelers can rest and enjoy a few hours of sunbathing, boating, swimming, and picnicking. Fishing is also available at the beach.

Havre De Grace, Maryland

Heading back to Maryland, Havre De Grace is a charming town situated along the shore where the Chesapeake Bay meets the Susquehanna River. Start a trip here off on a relaxing note with a stroll down the Havre de Grace Promenade. The 3/4 mile stretch of boardwalk provides pristine views of the Susquehanna River and the various waterfowl that call this area home. The Promenade is also located within walking distance of some of the town's other main attractions including the adorable Concord Point Lighthouse and the Decoy Museum. At the museum, visitors can learn about the art of decoy-making while discovering how decoys are integral to the Chesapeake Bay area. Finally, head to Susquehanna State Park where activities such as mountain biking, hiking, fishing, and camping are all available.

Solomons Island, Maryland

Solomons Island, Maryland is a charming little town located just over 100 miles from Havre De Grace. The island, known to be a “quaint destination for water lovers,” features a range of interesting activities both on and off the water. Art lovers can head to the AnnMarie Sculpture Garden to admire all kinds of natural and manmade beauties. Next, head to the Calvert Marine Museum. Here, visitors can enjoy the exhibits, take part in regular events, catch the occasional concert, wander the Marsh Walk, and see all kinds of marine animals.

Finally, wrap up the visit with a ride on the Cruisin Tikis. The tiki-themed tour is one of the best ways to see Solomons Island and promises cold drinks, island vibes, and good music.

Wrapping Up

From history buffs who can’t get enough of the local maritime museums to water enthusiasts making a splash at Cape Charles Beach, the Chesapeake Bay area is a wonderland of fun. So pack up your swimwear and fishing gear and get ready to soak up all that these small Chesapeake Bay towns have to offer.