Religious Freedom

America’s roots of religious tolerance run deep in Southern Maryland, where some of the nation’s oldest churches are an indelible part of this peaceful, small-town landscape.

St. Ignatius Catholic Church is one of the oldest parishes in the United States. The church was founded by English Jesuit Father Andrew White who arrived at St. Clement's Island on the Ark and the Dove in 1634 and celebrated the first Mass in what became Maryland.

Southern Maryland
189 miles from Port Tobacco to Point Lookout on country roads and distinguished Main Streets

Places along the way

When English settlers — Protestant and Catholic alike — sailed up the Chesapeake Bay in the 1600s, they brought with them the belief that individuals had the right to hold dissenting religious opinions. Today you can follow their spiritual journey through this tidewater region and along the shores of the Potomac River. Particular emphasis is placed on Historic St. Mary’s City, often recognized as “the birthplace of religious toleration in North America.”

Port Tobacco Loop

Including MD 6, MD 425 & MD 224

The byway begins in Port Tobacco, originally a Potapoco Indian village where Jesuit Father Andrew White established a missionary outpost. Visit the one-room schoolhouse built in 1872 and tour the Port Tobacco Courthouse, now a museum containing tobacco exhibits and archaeological finds.

Continue west, stopping at the Christ Church Durham Parish. Though the parish dates to 1692, the current brick structure was constructed in the 1730s. Next is Smallwood State Park, which houses the estate of Gen. William Smallwood, a Revolutionary War hero and the fourth governor of Maryland. There is also a marina and excellent fishing opportunities, as evidenced by the number of national bass-fishing competitions that have been held here.

More fishing is available on a 23-acre lake inside the Myrtle Grove Wildlife Management Area. Then, as you head back to Port Tobacco, be sure to stop by the Mt. Carmel Monastery, which was established in 1790 as America’s first religious community for women.

The last stop on this portion of the byway is the 322-acre Thomas Stone National Historic Site, which is also part of an 830-mile Potomac Heritage National Scenic Trail that stretches between the Chesapeake Bay and the Allegheny Highlands. Take a guided plantation tour to learn about Stone, who was one of four signers of the Declaration of Independence to hail from Maryland.

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Look for special events in the Leonardtown Arts and Entertainment District, such as Plein Air Painting.

Photo By: St. Mary's County

Chapel Point to St. Clement’s Island

Including MD 234 & MD 238

Go south toward Chapel Point to visit the oldest continuously serving Catholic parish in the nation, St. Ignatius Catholic Church, which was established by the Jesuits in 1641. Nearby is St. Thomas Manor, which was constructed a century later and is the oldest Jesuit residence in the world still in use.

Travel east through Zekiah Swamp Natural Environment Area to reach Chaptico, a port town that was occupied by the British during both the American Revolution and the War of 1812. Christ Episcopal Church, King and Queen Parish, was built here in 1736 on land donated by Francis Scott Key’s grandfather. The church is open to the public for tours, and visitors are encouraged to enjoy the annual strawberry and fall festivals.

Branching off the main byway, head south to Coltons Point and the St. Clement’s Island Museum, which features exhibits on Maryland’s earliest history and serves as a launching point for water taxi rides to the island itself. St. Clement’s Island is where Father White celebrated the first Roman Catholic Mass in the colonies. Today, the island is a state park on which a 40-foot-tall cross honors those first colonists who, in 1634, conceptualized the separation of church and state.

Chaptico to Point Lookout

Including MD 234, MD 243, MD 5 & MD 249

Continuing past St. Francis Xavier Church, the oldest Roman Catholic Church in the state, you enter the heart of Leonardtown. Be sure to visit both the Old Jail Museum, a tourist information center that also contains early Maryland artifacts, and Tudor Hall, a 250-year-old Colonial House now operated by the St. Mary’s County Historical Society.

The next stop is St. George’s Episcopal Church, which has held services since 1638, making it the oldest Episcopal parish in Maryland. Continue south to visit Piney Point, the site of the Piney Point Lighthouse, the oldest lighthouse on the Potomac River. From there, make your way to St. Mary's College of Maryland, a female seminary that was established in 1840, which now is a co-educational state college and hosts a weekly summer concert series.

Probably the most visited destination on this byway is Historic St. Mary’s City, an expansive living-history museum and archaeology site. Serving as Maryland’s first capital from 1634 to 1695, St. Mary’s City was the fourth permanent settlement in America and site of the first Catholic chapel in the colonies. Exhibits include a reconstructed 17th-century State House, a tobacco plantation, an Indian hamlet and a replica of the Maryland Dove, one of the two square-rigged ships that brought the first settlers to Maryland. 

Heading toward the Chesapeake Bay, you can see several lighthouses and visit Point Lookout State Park, which offers beaches, a boat launch, fishing areas and campgrounds. But there’s another side to this picturesque peninsula — during the Civil War, Point Lookout served as a notorious prison camp where more than 4,000 Confederate soldiers died. Ghost stories abound, bringing a haunting conclusion to this spiritual journey.

Point Lookout State Park in Scotland provides sweeping views of the Chesapeake Bay and a chance to paddle, fish or swim.

Photo By: St. Mary's County

Maryland Lore

The Freedom of Conscience Monument, which sits at the entrance to Historic St. Mary’s City, was erected nearly 80 years ago to commemorate a 1649 Act passed by the General Assembly that mandated religious tolerance of all Trinitarians, laying the foundation for the First Amendment to the U.S. Constitution.

Experience the 17th century at Maryland's first capital - Historic St. Mary's City. Interactive and participatory displays at the village provide a glimpse into the lives of English settlers who sought democracy and toleration. 

Photo By: Historic St. Mary's City

Byways in this Region

Roots & Tides
Booth's Escape

Byways Guide & Map

Maryland Scenic Byways Travel Guide and Map

Learn more with our FREE Maryland Scenic Byways Travel Guide & Map Start planning your road trip with our official guide and map.