Historic Sites in Southern Maryland

3 Actors standing outside in the sunlight in 17th Century Garb

Step into the shoes of early settlers as you walk through these historic destinations.

Start: Historic Sotterley

Finish: Point Lookout State Park

Distance: 1 day, 4 stops, 36.2 miles

Slave quarters at Sotterley Plantation in Hollywood, MD. Photo Credit: Heidi Schlag

STOP 1

Historic Sotterley

44300 Sotterley Ln, Hollywood, MD 20636

We start our historic road trip at Sotterley Plantation in Hollywood. A National Historic Landmark and a UNESCO Site of Memory for the Slave Route Project, this site encompasses over 300 years of history. English planter James Bowles built a two-room home on the site by 1703, and subsequent family members expanded the structure. On weekends, the mansion is open for tours, and a virtual tour is available on the Clio mobile app.

STOP 2

The Old Jail Museum & Leonardtown Visitor Center

41625 Court House Dr, Leonardtown, MD 20650

Our next stop is Leonardtown, a historic, waterfront town mixed with modern appeal. Check out the Old Jail Museum in operation until 1945 by the oldest sheriff’s office in the nation and the Leonardtown Visitor Center. Notable exhibits include the recently unveiled Benjamin Hance Historic Marker in conjunction with the Equal Justice Initiative honoring the 1887 lynching victim. If folklore is more your speed, tempt the fates at alleged witch Moll Dyer’s Rock.

A man listening to two historical reenactors — Photo Credit: Heidi Schlag

STOP 3

Historic St. Mary’s City

18751 Hogaboom Ln, St Marys City, MD 20686

Carve out some extra time to explore Historic St. Mary’s City–a museum of living history and archaeology. St. Mary’s City was where Maryland got its start, when in 1634, Leonard Calvert and 140 settlers staked their claim. Of course, they weren’t alone on these shores, as the museum reminds us at the Woodlawn Indian Hamlet, where they tell the story of the Yaocomaco people and neighboring tribes. St. Mary’s City interpreters dress in costume but converse in the third person and teach guests how to play games of the settlers.

room with bunks and table — Photo Credit: Courtesy of Visit St. Mary’s MD

STOP 4

Point Lookout State Park

10350 Point Lookout Rd in Scotland, MD 20687

Located on a small peninsula at the confluence of the Potomac River and the Chesapeake Bay, Point Lookout offered guidance for mariners and housed Civil War prisoners. The civil war brought death and destruction to Point Lookout’s beautiful beaches. What began as a hospital for Union soldiers quickly expanded into the Civil War’s largest prison camp, at one point housing 20,000 prisoners. Due to the traumatic death toll of war and shipwrecks off shore, the Point Lookout lighthouse is said to be haunted and is the subject of many paranormal investigations.

Lead Photo: Historic St. Mary’s City

Content originally featured in “3 Days of Historic Exploration in Southern Maryland” by Heidi Schlag