7 Undiscovered Small Towns in Chesapeake Bay

The historic Chesapeake Bay is the largest estuary in the United States, covering parts of Maryland, Virginia, and Delaware. The region is known for its maritime history, and the small towns that make up the region are exemplary. Historic downtowns and bayside architecture make these towns unique, as do the sites and historic structures.

This region has many cultural interests, including museums, art galleries, and performing arts theatre. The cooler months are ideal for exploring on self or docent-guided walking tours, and the food scene is just as exciting. Here are seven undiscovered towns in the Chesapeake Bay.

Havre de Grace, Maryland

Havre de Grace is an idyllic town at the mouth of Maryland's Susquehanna River. The town is notable for its parks, historic sites, and waterfront scenery. Concord Point Park is home to the landmark Concord Point Lighthouse, and David Craig Park, offering spectacular views of the Susquehanna River. The downtown area is also charming, with boutiques and other attractions.

The Main Street community has public art displays, including a mural of Bald Eagles and the stainless steel Big Fish School of Fish. Museums include the Havre de Grace Maritime Museum, the Steppingstone Farm Museum, Concord Point Lighthouse, and Keeper's House Museum. Discovering this charming town by walking around is perhaps the best way to take all its delights.

St. Michaels, Maryland

The small coastal town of St. Michaels is packed with charming points of interest that epitomize Chesapeake Bay's character. The 18-acre Chesapeake Bay Maritime Museum contains interactive exhibits and an 1879 Hooper Strait Lighthouse detailing the town's history. Talbot Street maintains quaint shops and some of the best restaurants in the area.

Millions of oysters have been offloaded at the waterfront St. Michael's Crab House. The chef-inspired menu specializes in oysters and other classic coastal dishes. There are several award-winning restaurants in St. Michaels. The Limoncello Wine Bar and Restaurant, Blu MIles Seafood and Grill, and Ruse Restaurant are popular choices.

Cambridge, Maryland

Cambridge, Maryland, is a classic bay town with an artsy atmosphere and a historic downtown area. It was founded in 1684 and is one of the oldest colonial towns in Maryland. Several museums, like the famed Harriet Tubman Underground Railroad Byway, showcase the town's maritime and agricultural history. Besides the historical sites, Cambridge has a lot of things to see and do.

The 40-acre historic district stretches along the coast and encompasses downtown, where many distinguished businessmen once lived. The brick storefronts lend Main Street a nostalgic feel, and the community comes together for several annual live events. The Taste of Cambridge celebrates the local cuisine with a street festival held every October. Cambridge has many points of interest that make it one of the best towns to discover in the Chesapeake Bay.

Chesapeake City, Maryland

The historic town of Chesapeake City is the only town in Maryland with a working commercial canal and is known for its 19th-century architecture. Cultural attractions include the Chesapeake City Museum, which features a collection of memorabilia and exhibits showcasing the town's history, specifically its Ukrainian heritage.

Pell Gardens is a romantic park in the downtown area. The historic park has quaint views of the canal, and two celebration venues are commonly used for weddings. Several historic inns are available to book a room. The Blue Max Inn, Inn at the Canal, and the Shipwatch Inn are stunning in their beauty and views. Each inn combines modern amenities with antiques and wrap around porches within walking distance of the waterfront.

Oxford, Maryland

Oxford is a beautiful waterfront village in Maryland known for its tree-lined streets and one of the oldest towns in the United States. The former Colonial port has retained its historic architecture while incorporating modern boutiques and some of the best culinary treats in the US. Mystery Loves Company Booksellers downtown sells mystery books taking place in the Chesapeake Bay area, a fun foray into local history. Strolls through the historic districts are quintessential for soaking up the cultural heritage of Oxford.

The 19th-century Victorian Nichols House Cottage is available for booking and within walking distance of the historic sites, restaurants, and cultural interests. The 1880 Oxford Inn is a comfortable inn that faces east so guests can witness spectacular sunrises. A short distance away is the Oxford-Bellevue Ferry along one of the oldest roads in the country.

Cape Charles, Virginia

The historic town of Cape Charles, Virginia, boasts the most extensive collection of early 20th-century homes on the East Coast. History and architecture buffs will fall in love with the town, and outdoor enthusiasts will enjoy kayaking, fishing, and hiking trails. Among the historic sites is the Cape Charles Museum, with exhibits highlighting the town's railroad history. The alluring downtown area is packed with historical buildings and is a great way to spend an afternoon.

Historic residences include Eeyre Hall, which has been in the same family since 1760. The Custis Tombs honors one of the earliest settlers of Virginia with an ornately decorated monument to the Custic family and their family crest. Sailing ships and other forms of water transportation are available for guided tours and views of the historically significant Cape Charles.

Onancock, Virginia

The port town of Onancock, Virginia, was founded in 1608 and is today known for its artistic flare. Artists, sculptors, and painters flock to the town for its natural scenery. Galleries like the Red Queen Gallery and Studio 117 showcase the works of renowned local artists. The galleries and studios are near several historic bed and breakfasts, the best way to spend a night in town.

The Inn at Onancock is a Victorian residence well-preserved with modern amenities. The 1890 Spinning Wheel Bed and Breakfast was the first in Onancock. The Inn offers appropriate themed rooms, each painted a different color. Onancock is a traditional Eastern port town with lovely sites and historic architecture that offers many things for visitors to discover.

Conclusion

Chesapeake Bay is a gorgeous and historic region with celebrated museums, historical sites, and first-rate coastal cuisine. Many of these towns are designated Main Street communities, and discovering the vintage architecture is only one of the many joys they offer. The maritime history is prevalent, for good reason, but there is also a storied colonial and agricultural history.

Cambridge's history dates back to 1684 and has played a significant role in the agricultural and maritime businesses. Havre de Grace has a rich history, including its 19th-century lighthouse and museum. The award-winning restaurants, points of interest, and cultural influences make these towns some of the best in the coastal region.