View of Chesapeake City from the Chesapeake City Bridge, Maryland.

7 Little-Known Towns On The Chesapeake Bay

Chesapeake Bay is a popular area to visit because of the beautiful vistas. The rolling hills and serene rivers flowing into the bay draw people in to admire the natural scenery of the area. This makes the Chesapeake Bay a popular summer destination. While cities such as Baltimore usually get most of the area's tourist attention, it is full of charming small towns. The small towns offer a less crowded experience of Chesapeake Bay. In Oxford, Maryland, for example, there are private sandy beaches to enjoy under the sun. Here, we explore seven little-known towns on the Chesapeake Bay.

Cape Charles, Virginia

Bay Creek at dusk in Cape Charles, VA.
Bay Creek at dusk in Cape Charles, VA.

Located on Virginia's Eastern Shore, Cape Charles is a sleepy town with a rich history and quiet beaches. The historic district is a must-see in Cape Charles. In 1991, it was placed on the National Register of Historic Places. Walking around the town's historic district is a great way to learn about the history of the area. In the 1880s, Cape Charles shipped goods across Cape Charles from the Delmarva Peninsula. The Historic District has 526 buildings and three other structures, including public beaches and piers to enjoy. Learn even more about Cape Charles's history at the local Cape Charles Museum. To see a unique structure, head over to Smith's Island to see Virginia's tallest lighthouse. While it's no longer in service, the lighthouse is so tall it's a site to behold. Nature lovers will enjoy walking in Kiptopeke State Park. In the winter, migratory birds pass through the area, making it a great spot for bird watching.

Chesapeake City, Maryland

Chesapeake City, MD, USA. Editorial credit: George Sheldon / Shutterstock.com
Chesapeake City, MD, USA. Editorial credit: George Sheldon / Shutterstock.com

Imagine spending a day exploring museums, walking through beautiful parks and trails, and stopping for an outdoor concert. This is what you can expect to find in Chesapeake City, Maryland. The small town is just over an hour from Baltimore, making it a great place for a weekend getaway from the city. Learn about the town's past and see artifacts from early settlers of the area at The Chesapeake City Museum. Walk through the downtown and admire the buildings still standing from the 1800s. On the southern bank of the canal, the historic downtown is on the Maryland and National Historic Registries. Here, you will see well-preserved 19th-century buildings. Since Chesapeake City is on the Chesapeake & Delaware Canal, it is a great place for a relaxing boat ride down the canal or a cruise. A few companies in the town offer sightseeing cruises where you can drink mimosa and enjoy the sights of the town from the serene water. Those who want to admire the Chesapeake & Delaware Canal without venturing into the water might enjoy the Ben Cardin C&D Canal Trail. The trail is a paved 15-mile pathway that runs from Chesapeake City to Delaware City and is perfect for a bike ride.

Williamsburg, Virginia

Governor's Palace in Colonial Williamsburg, VA.
Governor's Palace in Colonial Williamsburg, VA.

Full of historic charm, Williamsburg is a small town in Chesapeake Bay that brings the past to life. Walking around the town, you will see numerous historic buildings that bring you back to the past, including the Governor's Palace. This gives visitors a look at life as an 18th-century aristocrat. Wander around inside and see the lavish décor and period furniture. The Jamestown Settlement is another interesting historic site in town, bringing back to life the first permanent English colony in the area. Here, you can walk through a Powhatan village and see a colonial fort with people in costume, which displays an interpretation of 17th-century life. If you want to find something from the past to take home with you, stop at Williamsburg Antique Mall. There are over 300 vendors with antiques ranging from furniture to jewelry. Afterward, stop at Raleigh Tavern. The historic building was the hub of social events in the 18th century. Today, it has been turned into a charming café, but its historic charm is preserved in the atmosphere. Rent a bike to explore the area's natural beauty on the Colonial Parkway and Jamestown Island Loop trails. Biking is a great way to enjoy the sites of the town.

Yorktown, Virginia

The Nelson House was the home of Thomas Nelson, Jr. Editorial credit: William Silver / Shutterstock.com
The Nelson House was the home of Thomas Nelson, Jr. Editorial credit: William Silver / Shutterstock.com

Yorktown is a charming town best known for its history. Learn about it for yourself at the Yorktown American Revolution Museum. Afterward, walk along the Yorktown Riverwalk Landing that leads to Yorktown Beach. Many events happen on the Riverwalk throughout the year, and there is even a restaurant called Water Front Grill. Once you get to the beach, enjoy the peaceful waters and read a book on the shore or splash around in the water. A block up from the beach is the historic Main Street. Here, you will find historic homes, charming bed and breakfasts, and churches. Three must see buildings o this strip include Custom House, Nelson House, and The Digges House. All these homes are from the 1700s and have their own story to tell.

Havre De Grace, Maryland

Havre De Grace city illuminated by the golden light of dusk. Editorial credit: Wirestock Creators / Shutterstock.com
Havre De Grace city illuminated by the golden light of dusk. Editorial credit: Wirestock Creators / Shutterstock.com

Havre De Grace is one of Maryland's prettiest towns. Sitting on the Susquehanna River, there are numerous stunning views to admire throughout the town. For a pretty walk and a mini history lesson, walk along the Havre De Grace Promenade. The boardwalk winds from Tydings Park to Concord Point and has interpretive signs to learn about the historical significance of the area. The boardwalk stretches to the foot of the Concord Point Lighthouse. One of the town's staple landmarks. Just upstream from the town is Susquehanna State Park. The park has 15 miles of trail to explore and intriguing historic sites in the Rock Run Historic Area, including the Rock Run Grist Mill and a fragment of the Susquehanna and Tidewater Canal.

Solomons Island, Maryland

Hexagonal Drum Point Lighthouse at the open-air Calvert Marine Museum. Editorial credit: LEE SNIDER PHOTO IMAGES / Shutterstock.com
Hexagonal Drum Point Lighthouse at the open-air Calvert Marine Museum. Editorial credit: LEE SNIDER PHOTO IMAGES / Shutterstock.com

Close to Washington and Baltimore, Solomons Island is a great weekend escape from the city. The town has several unique sites, including the Annmarie Sculpture Garden and Arts Center. The gallery is on 30 acres of landscaped grounds and features 30 artworks. To see more art, visit Carmen's Gallery. The gallery displays art from local and international artists. Nearby, check out the Calvert Marine Museum, which protects a unique part of Solomons Island's history: the screw-pile lighthouses. These were initially built in the 1850s at Drum Point as a guide at the entrance of the Patuxent River. In 1962, the lighthouses were replaced by offshore lighthouses. The Calvert County Historical Society repaired and restored one of the screw-pile lighthouses and opened the lighthouse as a historic exhibit at the local museum for the public to see. Another exciting attraction in Solomons Island is the Calvert Cliffs. Just outside the town, the two-mile hike takes visitors up to a chalky white cliff by the Chesapeake Bay. The cliff is a beach popular amongst fossil hunters. Here, you can relish the area's natural beauty and maybe find a fossil or two to take home.

Oxford, Maryland

Oxford, Maryland, USA. Editorial credit: JE Dean / Shutterstock.com
Oxford, Maryland, USA. Editorial credit: JE Dean / Shutterstock.com

Oxford, Maryland, is a dreamy town with cute shops, bike trails, and museums. Oxford's Premier Bike Trail is one of the best biking trails in the Mid-Atlantic region. The route takes riders through the historic town of Oxford and the crossroads of Royal Oaks, with antique shops and a cute post office. On your ride, stop in at the Mystery Loves Company Bookstore. The unique shop is full of mystery books and has a great selection of regional titles. Later, check out the Oxford Museum, which documents 300 years of American and colonial history in the area. Oxford is also home to one of America's oldest ferries, the Oxford Bellevue Ferry. Take a trip down the Tred Avon River on the 341-year-old ferry. Unwind and enjoy the calm waters and colonial-era town.

Overall, while these small towns are underrated and overshadowed by bigger cities such as Baltimore, their charm and natural beauty are unparalleled. In Yorktown, you can enjoy the natural beauty of Chesapeake Bay on a quiet beach. Solomons Island has unique historical attractions, including a screw-pile lighthouse and a unique beach to hunt for fossils. Whether you are looking to learn about history or enjoy the natural charm of Chesapeake Bay, these towns make a great vacation destination.

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