8 Old-World Towns to Visit in Maryland

Founded in 1634 and shaped by Chesapeake Bay waterways like the Potomac, Maryland developed many small towns that still feel old-world. Annapolis carries that legacy forward as the state capital, with attractions like the Annapolis Maritime Museum and nearby Historic London Town adding depth to its centuries-old waterfront setting. Hagerstown reveals another side of Maryland’s past, with Civil War landmarks such as the Antietam National Battlefield and the National Museum of Civil War Medicine, along with access to the 184.5-mile Chesapeake & Ohio Canal. For a fun and informative journey through Maryland’s past, these eight towns showcase some of the state’s most rewarding towns.

Hagerstown

Hagerstown's colonial history dates back to 1739 when German immigrant Jonathan Hager bought 200 acres in the area. Later, its strategic location between the North and South made it a key site during the American Civil War. Today, the town has about 43,500 residents and features many preserved Civil War sites, such as the Antietam National Battlefield, where the bloodiest one-day battle in the country’s history took place, 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 in operation for around 100 years.

Salisbury

Salisbury began 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 shares Salisbury’s history, dating back to 1741 when one of the town’s founders built Pemberton Hall, which still stands on the park grounds today. Many of the town’s agricultural traditions have been preserved by residents, and visitors can explore them 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 restored rooms.

St. Michaels

Saint Michaels was officially incorporated as a town in 1804 and later played a role in the War of 1812, including hosting the Battle of Saint Michaels. The Saint Michaels Museum on St. Mary’s Square features a new exhibit about Saint Michaels in 1813, offering insights into its wartime history. Visitors can also embark on a self-guided walking tour to explore some of the town’s historic sites, such as 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 to the Saint Michaels harbor and the nearby Miles River to kayak, sail, or enjoy a river cruise.

Havre de Grace

Havre de Grace has historic 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 explore, such as The Lafayette Trail, a self-guided walking tour that shares 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 wanting 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 historic district with well-preserved colonial houses to explore. 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 be home to 5,300 residents. Nearly 50 structures throughout town are listed on the National Register of Historic Places, representing the Federal, Victorian, and 20th-century periods. The Calvin B. Taylor House Museum is especially worth visiting, as it is an early 1800s home with historic furnishings and memorabilia on display. Another way to explore the city is by booking a Rail Bike Tour, which passes through the town’s historic district, nearby coastal forests, and farmland.

Annapolis

Annapolis, situated on Chesapeake Bay, became Maryland's capital at the end of the 17th century. Today, it ranks as one of the ten smallest state capitals nationwide, with roughly 40,600 residents. Just eight miles from downtown, visitors can explore Historic London Town, which offers historic houses, a woodland garden, and ornamental gardens. The Annapolis Maritime Museum and Banneker-Douglass Museum, the state’s official museum for African American heritage, also showcase the region’s history. To learn more about the local ecosystems, Jug Bay Wetlands Sanctuary features 1,600 acres of wetlands, meadows, and forests for visitors to explore and observe native wildlife.

Boonsboro

Boonsboro was incorporated as a town in 1831, becoming a significant site during the American Civil War. The Boonsborough Museum of History houses a large Civil War collection, including artifacts from the Antietam and Gettysburg Campaigns. Visitors can also stop at the William Boone Family Gravesite, where one of the town’s founders is buried. Those interested in canoeing, swimming, or fishing can visit 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.