7 Must-See Historic Sites In Southern Maryland

CALIFORNIA, Md. — Southern Maryland is home to St. Mary’s County, the first established community in the state of Maryland. Calvert and Charles counties also offer a wealth of American history to explore, and there are ample locales that can act as a time machine to centuries past.

The Southern Maryland National Heritage Area recently released a list of historical locations to visit around Southern Maryland, and we’re offering up a few fun facts about each of the places that helped build our state into what you see today.

Historic St. Mary’s City

The most famous location on the list, Historic St. Mary’s City, is one of the most important locales in the history of Maryland. Once the capital of Maryland before Annapolis took its place, St. Mary’s City was the first settlement in the Old Line State, dating back to 1634.

In the modern day, Historic St. Mary’s City is an expansive museum-like experience, complete with reenactors and many unique exhibits that explore the life of the settlers who lived in Maryland hundreds of years ago.

Address: 18751 Hogaboom Lane, St. Marys City, MD 20686

Historic Sotterley

The Historic Sotterley plantation acts as an educational asset to teach contemporary people of Maryland about the region’s past relationship with complex issues like slavery. Notable exhibits include the Slave Quarters, Land, Lives, & Labor, and the Middle Passage Marker.

Once a major plantation in St. Mary’s County, this museum serves to help people of the modern day digest the realities of the residents and their day-to-day lives. Located on the Patuxent River, the Historic Sotterley plantation even features a manor dating back to 1703.

Address: 44300 Sotterley Lane, Hollywood, MD 20636

Maxwell Hall

Maxwell Hall was built in 1768 by George Maxwell, a tobacco farmer who was also known as a merchant. This Charles County location is famous for its connection to the War of 1812 and its distinct 18th-century architecture.

In the modern day, Maxwell Hall Park has added a variety of fun features for Marylanders who purchase an annual membership for $25, namely a host of different trails for horseback riding. Hikers can also explore the location for an exciting walk through a land rich with history.

Address: 6680 Maxwell Drive, Hughesville, MD 20637

Port Tobacco

Port Tobacco was founded in 1727 and was once the second-biggest city in Maryland, though it’s currently home to just a handful of people. In its day, Port Tobacco was known for exporting tobacco and importing items from European countries.

The Historic Port Tobacco Village presently acts as a place for visitors to explore, either by themselves or through an exciting tour. Stagg Hall and the Port Tobacco Courthouse are just a few of the exciting buildings you’ll learn about on your adventure in Charles County, so it’s worth a trip if you love history.

Address: 8430 Commerce St., Port Tobacco, MD 20677

Smallwood Retreat House And State Park

The Smallwood Retreat House was once the home of William Smallwood, a general during the Revolutionary War who held the position of highest-ranking military man in Maryland throughout the war. Smallwood was also the governor of Maryland, cementing his legacy in the state.

Now a state park in Charles County, Smallwood Retreat House is a fun choice for hiking in the Southern Maryland area. Picnic areas and playgrounds are also available, so William Smallwood’s historical house is now surrounded by a variety of family-friendly activities.

Address: 2750 Sweden Point Road, Marbury, MD 20658

St. Clement’s Island

St. Clement’s Island is where the first Maryland settlers founded the Old Line State after they landed in America in 1634. Acting as a temporary home for the original British settlers, this island is one of the most important sites in the entirety of Maryland’s history.

Once a temporary community, St. Clement’s Island has since been turned into a state park where visitors can explore a replica of the Blackistone Lighthouse and other interesting sights. The St. Clement’s Island Museum offers water taxis to the park, allowing interested Marylanders to travel to the island, which is situated on the Potomac River.

Related Article: Groundbreaking For A New St. Clement’s Island Museum, Preserving Maryland’s Origins With A Complete Narrative

Address: Under construction as of September 2025

The Thomas Stone House

Thomas Stone is one of the 56 men who took part in signing the Declaration of Independence due to his contributions during the American Revolutionary War. As such, he is revered in Maryland history for his importance to the United States and its founding.

Today, the Thomas Stone National Historic Park has solidified Stone’s impact on America by offering guided tours of his home and trails to explore, one of which features the Stone Family Cemetery.

Address: 6655 Rose Hill Road, Port Tobacco, MD 20677

Itching For More Maryland History?

If you want to learn more about Maryland’s extensive history as one of the first states founded in America, read up on the past of St. Mary’s County or the most notable people born in Maryland.

---