These Small Towns on Chesapeake Bay Have the Best Historic Districts
The Chesapeake Bay is one of the most biologically unique bodies of water on the planet. The name, from the Algonquin language, is the seventh-oldest English place name in the country. Early European expeditions found varieties of crab enjoying the estuary’s rare tidal treats. Some small Chesapeake towns have retained more of the history that passed through it than others. Escape to the still thriving towns of the Chesapeake Bay, known for centuries among Epicureans as the Great Shellfish Bay. America’s best Historic Districts are a day trip away for residents in Maryland and Virginia.
Easton, Maryland
Easton, Maryland, has a population of 17,100 who never tire of their 900-building Historic District that has been on the National Registry of Historic Places since 1980. Check in with the Talbot Historical Society between Wednesday and Friday for photos and expertise of the entire county’s history. The oldest section of the Academy Art Museum was built in 1820. Today, their collection includes the likes of Rembrandt, Goya, and Picasso. Score tickets to a show at Avalon Foundation Inc., and try not to focus on the gorgeous interior of a historic 1921-built theater originally intended as a cinema.
Havre de Grace, Maryland
Saunter the ¾ mile promenade for a sneak preview of the historic and scenic treasures of the population-14,800 town of Havre de Grace. Nearly 1,000 buildings make up the historic downtown area, which was added—as a whole—to the National Registry of Historic Places in 1987. The Friends-Concord Point Lighthouse began illuminating where the Susquehanna River meets the Bay in 1827. Visit the Havre de Grace Maritime Museum to get caught up on the Chesapeake’s natural, cultural, and social history. Susquehanna State Park is handy for a getaway into nature.
Gloucester, Virginia
Gloucester is the seat of the county of the same name. There are around 3,000 residents in Gloucester, but the county’s population is just above 39,000. The Gloucester Downtown Historic District spans 57 architectural gems. Expect others from the county to show up for the town’s famous annual events, such as the Daffodil Festival. The building that houses the Gloucester Museum of History was built in 1770. It was once a tavern that serviced weary travelers on their way to the Gloucester Courthouse. Machicomoco State Park’s interpretive pavilion informs visitors about the region’s rich history before the arrival of European settlers. Do not forget to stock up on treats at Northern Neck Popcorn Bag before leaving.
Edgemere, Maryland
Approximately 8,600 people live in Edgemere. The Craighill Channel Lower Range Rear Light Station was added to the National Registry of Historic Places in 2002. It is home to several Chesapeake maritime treasures, most notably Poole’s Island. The island is not accessible after being used for shelling practice for a succession of 20th-century wars. Spot the Poole’s Island lighthouse, lit in 1825 and still Maryland’s oldest, from the safety of a boat tour. Bring binoculars to appreciate Fort Carroll, which became a place that time forgot after disastrous flooding. The lighthouse and fort were used to store mines during the Spanish-American War. Also nearby, get close to a historic gun battery and barracks at Fort Smallwood Park.
Cape Charles, Virginia
Travel back to the late 19th and early 20th centuries in Cape Charles’ Historic District. Just over 1,000 people get to share the bounty of the over 500 buildings on the National Registry of Historic Places. Dive into the town’s history at the Cape Charles Museum, which hosts special events for the wider region. Cape Charles has inspired individuals and creatives for generations. See the fruit of their inspiration at Lemon Tree Art Gallery. The Gallery is also a hub for live music and community events. Visit the Eastern Shore of Virginia National Wildlife Refuge to experience the natural rhythms of animal migration that flourished long before Europeans arrived in the Chesapeake region.
Saint Mary’s City, Maryland
Saint Mary’s City was the first European settlement in Maryland. Visit the living museum between Tuesday and Saturday for friendly, costumed folk living the 17th-century life. Visit Point Lookout State Park and walk the thick planks over marshland, teeming with life, and gaze across the waters as some of the first European Americans did. Call ahead to ensure the boardwalk is not closed due to reaching capacity. The year-round population is around 1,000, but it swells by about 50% when students arrive in September. Bed-down in a historic spot at the Inn at Brome Howard with four unique, fully restored rooms.
Onancock, Virginia
Onancock’s history is vast. In the 1600s, Captain John Smith called it the "gem of the Eastern Shore." The population of 1,200 town loves to get together at the majestic 1921-built Historic Onancock School, which operates as a community center today. Check the school’s website for special events. Catch one of today’s flicks at the 1950s-era Roseland movie theater. Sleep in history at the boutique Charlotte Hotel, called the White Hotel, after it was built in 1907. Experience the local dramatic talent at the Northstreet Playhouse, which features year-round programming as well as a range of classes and theater camps for the young ones. The Onancock Historic District has over 250 contributing buildings.
The Chesapeake Bay’s unique biology means it is home to a variety of creatures, including the horseshoe crab, whose blue-tinged blood has allowed pharmaceutical companies to test the safety of their products for decades. Protect the bay that protects America by supporting kelp farming projects that clean the waters and feed its wildlife. Consider donating to the Chesapeake Bay Foundation and support Native American businesses in the area whenever possible. Well-preserved history is a privilege to experience. Help a Historic District’s beauty shine brighter by rectifying the wrongs of the past in which they were built.
