8 Old-World Towns to Visit in Maryland

Maryland has seen it throughout the country's history as one of the original 13 colonies and the site of numerous Revolutionary War, War of 1812, and Civil War events. Maryland’s small towns reflect its rich historical heritage, preserving war sites, artifacts, and 18th-century homes. Strolling through these small towns is like stepping back in time, where travelers can walk through the country’s journey and feel each era unfold around them.

Hagerstown

Hagerstown's colonial history traces back to 1739 when German immigrant Jonathan Hager purchased 200 acres in the area. Later, its strategic position between the North and South made it a key site during the American Civil War Today, the town is home to about 43,500 residents and has many Civil War sites preserved to visit, such as the Antietam National Battlefield, where the bloodiest one day battle in the country’s history, the Battle of Falling Waters 1863 Foundation, and the National Museum of Civil War Medicine. Visitors can also enjoy biking or walking along the Chesapeake & Ohio Canal, which is 184.5 miles long and has been operating for around 100 years.

Salisbury

Salisbury started off as a small colonial settlement in 1732 and was officially incorporated as a city in 1854. Today, nearly 33,200 residents call Salisbury home. Pemberton Historical Park tells a lot of Salisbury’s story, dating back to 1741 when one of the town’s founders built Pemberton Hall, whose structure remains on the premises of the park today. A lot of the town’s agricultural traditions have been preserved by residents as well, which visitors can explore during the annual Wicomico County Fair, which features livestock shows, rodeos, crocheting and embroidery lessons, and a pie eating contest among other events. Poplar Hill Mansion, one of Maryland’s oldest homes, is also worth a visit, offering tours of its beautifully refurbished rooms.

Saint Michaels

Saint Michaels was officially incorporated as a town in 1804 and later played a role in the War of 1812, hosting the Battle of Saint Michaels. The Saint Michaels Museum in St. Mary’s Square has a new exhibit on St. Michaels in 1813 to learn more about this wartime history. Visitors can also go on a self-guided walking tour to see some of the town’s historical sites, including the Navy Point, The Dodson House, the Dr. Dodson House, and The Colonel Joseph Kemp House. After learning about Saint Michaels’ history, travelers can head out the Saint Michaels harbor and the adjacent Miles River to kayak, sail, or enjoy a river cruise.

Havre de Grace

Havre de Grace has historical ties to the Revolutionary War, with war hero General Lafayette visiting the town multiple times. It was also the place where George Washington stopped before his first inauguration. Later, during the War of 1812, Havre de Grace became a target in a British raid. Today, the town of 15,000 has plenty of history and museums to appreciate, such as The Lafayette Trail, a self-guided walking tour that narrates the town’s history as visitors pass numerous buildings, the Havre de Grace Maritime Museum, and the Havre de Grace Colored School Museum & Cultural Center. Those who want to see a traditional lighthouse along the Chesapeake Bay can visit the Concord Point Lighthouse, built in 1827.

Chestertown

Established in 1706, Chestertown was one of Maryland’s original Royal Ports of Entry for the English. The town now has roughly 5,600 residents and a rich historic district with preserved colonial houses to see. The Historical Society of Kent County is a great starting point for those interested in colonial and Revolutionary history, offering ongoing lectures, exhibits, and a self-guided walking tour. Chestertown also hosts an Annual Tea Party Festival, featuring a reenactment of the 1774 tea dumping carried out by local residents. Craving a good craft beer? Bad Alfred’s Distillery in town serves beer, house-made spirits, and wood-fired pizza to enjoy.

Berlin

Founded as a 300-acre plantation in 1677, Berlin has grown over nearly three and a half centuries to become home to 5,300 residents. Nearly 50 structures throughout town are listed on the National Register of Historic Places, ranging from the Federal, Victorian, and 20th-century periods. The Calvin B. Taylor House Museum is particularly worth a visit, as a home from the early 1800s, complete with historic furnishings and memorabilia on display. Another way to explore the city is by reserving a Rail Bike Tour, which passes through the town’s historic district, nearby coastal forests, and farmland.

Annapolis

Annapolis, located on the Chesapeake Bay, became the capital of Maryland at the end of the 17th century. Today, it is one of the ten smallest state capitals in the country, with approximately 40,600 residents. Just eight miles from downtown, travelers can visit the Historic London Town, which features historic houses, a woodland garden, and ornamental gardens. The Annapolis Maritime Museum and Banneker-Douglass Museum, which is the state’s official museum for African American heritage, exhibit the region’s history as well. To learn more about the area’s ecosystems, the Jug Bay Wetlands Sanctuary has 1,600 acres of wetlands, meadows, and forests to explore and observe native wildlife.

Boonsboro

Boonsboro was incorporated as a town in 1831, becoming a key location in the American Civil War. The Boonsborough Museum of History is home to a large Civil War collection, including artifacts from the Antietam and Gettysburg Campaigns. Travelers can also visit the William Boone Family Gravesite, where one of the town’s founders is buried. Those looking to canoe, swim, or fish can go to Greenbrier State Park to enjoy its 42-acre manmade lake or go camping or hiking in South Mountain State Park, which connects to the Appalachian Trail.

Final Thoughts

Although many tourists opt to visit Washington D.C. to immerse themselves in the country’s history, there are so many small towns scattered throughout Maryland that can be equally intriguing. As one of the original 13 colonies and a key player in the Civil War, there is an abundance of history to explore in towns that people otherwise may typically pass up for larger nearby cities. If you’re ready to take a journey through the country’s history, one of these towns is the perfect place to start.