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
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.
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.
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.
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