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Old historic brick buildings and narrow streets in Berlin, Maryland. Image credit Kosoff via Shutterstock

8 Hidden Historical Towns In Maryland

Besides its stunning landscapes, framed by the Atlantic Ocean to the east and the Blue Ridge Mountains to the west, Maryland is a state steeped in history. It is one of the 13 original states, playing a part in several landmark events in America's past, from the American Revolutionary War and the Civil War to the Underground Railroad. This colorful heritage is well-preserved in little towns across the state, holding their histories close to heart.

Whether through museums, vintage homes, monuments, or old battle sites, they provide a vivid window into life as it was in the earlier years. From Civil War landmarks in Sharpsburg to the well-maintained historic district in St. Michaels, set the stage for an eye-opening trip down memory lane with a tour of these hidden historical towns in Maryland.

Cambridge

Marina in Cambridge, Maryland.
Marina in Cambridge, Maryland.

Cambridge is a quaint town on the Eastern Shore, known as the birthplace of Harriet Tubman and linked to Maryland's industrial and military histories. The community has immortalized Tubman at the Harriet Tubman Museum and Educational Center with educational exhibits about her life and legacy. Guests can explore rare artifacts depicting her iconic role during the Underground Railroad and watch a short film about her. Cambridge's location on the Choptank River has allowed it to amass a storied maritime heritage. This is reflected in the Choptank River Lighthouse, which was erected in 1870.

But for a deeper dive into the region's nautical history, you can visit the Richardson Maritime Museum. The venue harbors almost three centuries of Dorchester County's exploits on the Choptank River. It stores a fleet of model ships from the past, showcasing the craftsmanship of old-day boatbuilders.

Berlin

Rustic brick buildings in the downtown area of Berlin, Maryland.
Rustic brick buildings in the downtown area of Berlin, Maryland. Image credit Kosoff via Shutterstock

Berlin traces its origins to 1868, founded shortly after the Civil War. It preserves dozens of old buildings across the Berlin Commercial District, listed on the National Register of Historic Places. Notable sites in the neighborhood include Henry's Grove, and a tour provides a glimpse of late 18th-century Berlin. The home maintains its original structural integrity, portraying traditional building styles with its unique gable roof, brick walls, and interior detailing.

Another old building to check out is the St. Paul's Episcopal Church, established in 1825 to replace St. Martin's Church. Also, remember to spare a little time for a tour of the Rackliffe House on Assateague Island. This 1700s coastal plantation displays outdoor plaques about the homeowners and its history.

St. Michaels

Downtown street in St. Michaels, Maryland.
Downtown street in St. Michaels, Maryland. Image credit Chris Ferrara via Shutterstock

St. Michaels is one of Talbot County's oldest towns, with a history intertwined with trading and shipbuilding. According to the St. Michaels Museum, the community's beginnings date back to the mid-1600s, and much of its history comes to life at the St. Michaels Historic District. The corridor houses more than 300 contributing buildings that showcase diverse old-海角社区 architectural styles. Among these, the John Bruff House is one of the oldest standing structures in St. Michaels, boasting a heritage dating back to 1805.

Given its setting on the Chesapeake Bay and Miles River, St. Michaels has a storied maritime heritage. This is evidenced by the 1879 Hooper Strait Lighthouse, erected to illuminate the path for vessels navigating the dangerous waters of Hooper Strait. Furthermore, the Chesapeake Bay Maritime Museum displays an assortment of artifacts, relics, and old vessels related to the community's seafaring past.

Sharpsburg

The Town Hall and Library in Sharpsburg, Maryland.
The Town Hall and Library in Sharpsburg, Maryland. Image credit George Sheldon via Shutterstock

This sleepy town, less than 15 miles from Hagerstown, was founded in 1763 and has a captivating history steeped in the American Civil War. Sharpsburg famously hosted the Battle of Antietam, whose site is currently preserved at the Antietam National Battlefield. The battle is remembered for being exceptionally bloody, claiming or affecting 23,000 lives after just twelve hours of combat. Burnside Bridge is a notable landmark on the battlefield, built in 1836 to link Sharpsburg to Rohrersville. This iconic bridge was in the middle of the carnage during the war, which is hard to fathom given its quietness and serenity.

Almost 5,000 soldiers from the Union side of the conflict are buried at the Antietam National Cemetery. The location has a surreal atmosphere and draws tourists looking to pay their last respects to the fallen heroes.

Boonsboro

East Main Street, Boonsboro, Maryland.
East Main Street, Boonsboro, Maryland. Image credit Acroterion, CC BY-SA 4.0, via Wikimedia Commons

Boonsboro is approximately an hour from Baltimore and has a history dating back to 1792. It hosts a barrage of sites and markers from the formative years, but none more prominent than the Washington Monument. This rugged stone tower was constructed in 1827 by townspeople to honor the memory of President George Washington. However, it would also become a signal station during the Civil War.

A deeper look into Boonboro's past awaits at the Boonsborough Museum of History. Its extensive collection of exhibits features Civil War relics and archives from the Gettysburg and Antietam battles. Meanwhile, the Washington County Rural Heritage Museum depicts rural Maryland in the 1800s. It encompasses three museum buildings with artifacts about farming, transportation, and life at the time.

Leonardtown

Downtown Leonardtown, Maryland.
Downtown Leonardtown, Maryland. Image credit Elvert Barnes via Flickr.com

Leonardtown is a historic port town from the 17th century that hosted several vessels traveling on the Chesapeake Bay at its many steamboat landings in the 19th and 20th centuries. It houses numerous landmarks and sites throughout Historic Leonardtown, led by the Old Jail Museum. This granite and brick structure was constructed in 1876 and used until 1945, hosting the country's oldest sheriff's office. Tudor Hall is one of the town's oldest buildings and a standout in Historic Leonardtown. It dates back to the mid-1700s and sports a unique Georgian-style architecture.

Lastly, you can't miss the Moll Dyer Rock. This curious site goes back to the 17th century and preserves where a woman accused of witchcraft got stranded and froze to death. A rock on the site bears her handprint, and legend has it that those who touch the rock consequently start feeling dizzy.

Cumberland

Fall colors in Cumberland, Maryland.
Fall colors in Cumberland, Maryland.

Known for its picturesque views of the western Maryland mountains, Cumberland is also one of the most historical towns in Maryland. It was founded in 1787, becoming one of George Washington's first military headquarters. Walking down the Washington Street Historic District exposes a fair share of markers from the early days, including the gorgeous Emmanuel Episcopal Church from the mid-19th century. While there, remember to visit the Gordon-Roberts House for an idea of 1800s life in Cumberland. The rustic building belonged to a railroad baron and still holds on to furnishings and archives from the period.

For a unique historical experience, hitch a ride on the Western Maryland Scenic Railroad. This classic locomotive puts guests in the shoes of past passengers, taking them on an easygoing excursion through the mountainous backcountry.

St. Mary's City

Historic St Marys City, Town Center, St Marys County, Maryland.
Historic St Marys City, Town Center, St Marys County, Maryland. Image credit Malachi Jacobs via Shutterstock

St. Mary's City is the state's first European settlement and capital, with an enduring heritage from 1634. The colonial town was designated a living history site and displays multiple relics from Maryland's infant years. Some of the old buildings in the area include St. John's Site, which was built in 1638 by Maryland's first secretary. It houses original furnishings and artwork illustrating the evolution of the settlement through the 17th century. More old buildings from the 19th century are accessible at the historic St. Mary's College of Maryland, established in 1840.

The rustic Nancy R. & Norton T. Dodge Performing Arts Center welcomes guests for enthralling stage performances in its intimate interior. It is a recognized regional hub with a capacity of about 700 and hosts a lineup of concerts, plays, and musicals.

Maryland's riches go beyond its stunning natural scenery; it is one of the most historically significant Southern states. Naturally, one of the biggest draws for tourists is its colorful heritage, which shines in these historical towns in Maryland. From the European arrival in St. Mary's City to the Civil War in Sharpsburg, the state is a rich tapestry of American history that guarantees visitors a unique perspective of various events that shaped the United States.

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