6 Loveliest Small Towns to Visit in Chesapeake Bay This Summer

Chesapeake Bay, the largest estuary in the United States, is a natural treasure that spans over 200 miles, with the majority of it located in Maryland. Rich in history and crammed full of spectacular scenery, the region is a must-visit for any traveler looking for an authentic Mid-Atlantic coastal experience.

An area deeply rooted in American history, Chesapeake Bay attracts millions of visitors annually, many of them drawn by the region’s many charming small towns. Whether you are a day-tripper, a weekend warrior, or are here for a longer vacation, these six lovely small towns in the Chesapeake Bay are waiting to be visited this summer.

St. Michaels, Maryland

Located on Maryland’s Eastern Shore and only a 90-minute drive east of Baltimore, St. Michaels is a picturesque town known for its maritime heritage and quaint streets. Its position on the Miles River, which flows into the Chesapeake Bay, not only makes it a popular destination for boating and waterfront activities but certainly adds to its scenic charm. The river and its tributaries are especially fun for nature lovers as they’re ideal for kayaking and canoeing adventures. Those seeking land-based adventures will want to include the 2.5-mile-long St. Michaels Nature Trail on their itinerary for its peaceful woodland and wetland walks.

There is much to learn about the region at the excellent Chesapeake Bay Maritime Museum. Highlights include several historic vessels, interactive exhibits, and scenic views of the town’s harbor area, while the Hooper Strait Lighthouse provides fascinating details of the life of a Chesapeake Bay lighthouse keeper. It’s a sprawling property, so allow plenty of time to see everything. If planning a visit in the summer of 2024, consider taking in events like the St. Michaels BrewFest in June or the Watermen’s Appreciation Day on August 11; the latter celebrates the region’s seafaring heritage with a day of boat docking contests, live music, and delicious local fare.

Cambridge, Maryland

An easy 30-minute drive further south of St. Michaels, Cambridge is one of the oldest colonial cities in Maryland. Situated on the Choptank River, a good place to begin exploring Cambridge is the Dorchester County Visitor Center. In addition to stocking up on local info and travel tips, there’s plenty of parking, so ditch the car and enjoy a summer stroll along the riverfront and downtown area. This lovely Chesapeake Bay destination is also home to the Harriet Tubman Museum, a fascinating attraction that celebrates the life and legacy of the famed abolitionist and the Underground Railroad. In addition to offering a comprehensive look at Tubman’s life, displays also provide details of the Underground Railroad, a network that helped countless former slaves escape north.

Other great things to do in Cambridge include paying a visit to the Richardson Maritime Museum, and the nearby Blackwater National Wildlife Refuge. This vast preserve offers hiking, bird watching, and kayaking adventures and is known for its bald eagle population. Popular summer events include the Taste of Cambridge Crab Cook-Off, an annual event held in July that features crab dishes prepared by local chefs.

Chestertown, Maryland

Set on the banks of the Chester River, Chestertown is a great place to visit for those who enjoy exploring urban areas on foot. Start in Chestertown Historic District, home to numerous restored colonial and Victorian-era buildings and leafy neighborhoods that are perfect for a stroll. So, too, is the campus of Washington College, founded in 1782. A short stroll from the downtown area, it’s one of the oldest colleges in the United States and adds a youthful energy to the town.

Summer fun in Chestertown also includes visiting the Sultana Education Foundation which operates a historic schooner, the Sultana, a unique educational experience. Outdoor enthusiasts are well catered to here as well, with the nearby Eastern Neck National Wildlife Refuge being an excellent spot for bird watching, hiking, and exploring the diverse ecosystems of the Chesapeake Bay.

Havre de Grace, Maryland

Its location in the northwest corner of Chesapeake Bay at the mouth of the Susquehanna River makes Havre de Grace an ideal base from which to explore this beautiful part of America. This strategic position ensured the town’s importance as a maritime hub, with related must-sees being the Concord Point Lighthouse. One of the oldest continuously operating lighthouses in the United States, it’s now a museum with a Keeper’s House and gift shop. Havre de Grace Maritime Museum, a mural-covered attraction with exhibits on local shipbuilding and navigation, is also fun to visit.

Enjoy nature? Then head to Susquehanna State Park, an ideal spot for a summer visit for its network of hiking trails, picnic areas, camping, as well as fishing and boating. The Havre de Grace Promenade, a scenic boardwalk along the waterfront, is another excellent spot to spend a few hours in the summer. The Havre de Grace Seafood Festival on August 9-11 promises plenty of opportunities to experience delicious local seafood along with live entertainment and arts and crafts vendors, while the town’s Independence Day Celebration on July 4th includes a parade, fireworks, and various family-friendly activities.

Solomons, Maryland

Tucked away in the southwest corner of Maryland, Solomons (sometimes also referred to as “Solomons Island”) is situated at the mouth of the Patuxent River and makes for a great summer getaway destination. The Calvert Marine Museum is a must-visit attraction here, with exciting exhibits that explain the maritime history of the Chesapeake Bay. There’s also a small aquarium, while the historic Drum Point Lighthouse, built in 1883, is one of only three surviving “light stations” that once lined the Chesapeake Bay.

Nature lovers also won’t be bored with a summer visit to Solomons. Highlights include nearby Calvert Cliffs State Park, which is less than 10 minutes by car and famous for its dramatic cliffs, fossil hunting, and sandy beach. A popular late-summer event for art enthusiasts, the Solomons Plein Air Festival in September attracts artists from around the country to paint scenic landscapes of the area.

Oxford, Maryland

Located on Maryland’s Eastern Shore mid-way between St. Michaels and Cambridge, the scenic small town of Oxford is a lovely town that’s lauded for its historic charm and waterfront beauty. Its location on the Tred Avon River, which flows into the Chesapeake Bay, is a big plus and ensures the community is on the radar of boaters. Those without a boat needn’t worry as the Oxford-Bellevue Ferry, one of the oldest privately operated ferries in the United States, offers a scenic way to travel across the river.

The town’s historic district features some beautifully preserved colonial and Victorian buildings, too. Highlights include the Oxford Museum, located directly opposite Oxford Park, which is a great place to learn more about the town’s rich history, including its role in the oyster industry. Outdoors folks can spend their summer vacation here exploring the nearby Wye Island Natural Resources Management Area with its hiking trails, abundant bird life, and photo-worthy views over the Chesapeake Bay.

The Final Word

Chesapeake Bay’s loveliest small towns offer plenty of reasons for people to pay a visit. From the fascinating maritime heritage of destinations like St. Michaels and Solomons to the colonial-era communities of Chestertown and Oxford, each town provides a unique and authentic Chesapeake Bay experience. Whether you're exploring historic sites, enjoying waterfront activities, or participating in local festivals, these six lovely small towns in Chesapeake Bay are perfect for a summer visit.