Maryland’s Highways & Byways

(Photo courtesy of the Maryland Office of Tourism)

For a fairly small state, Maryland is bursting at the seams with scenic highways — 18 state byways and six national-designated scenic byways. Here are six of our faves:

Star-Spangled Banner

Journey back to the time of the War of 1812 and travel from Solomons Island in Southern Maryland to Baltimore’s Fort McHenry, where Francis Scott Key was inspired to write the poem that would become our national anthem during the Battle of Baltimore. This 106-mile route is part of the Great Chesapeake Bay Loop and provides ways to explore the authentic Chesapeake.

Fort McHenry
Fort McHenry (Provided Photo)

John Wilkes Booth: Chasing Lincoln’s Assassin

Follow the escape route of one of history’s most notorious assassins as he fled from Washington, D.C., and hid for weeks in Southern Maryland before being cornered by Union troops. This 66-mile trek starts at Ford’s Theatre and winds up in Pope’s Creek, Virginia, where Booth was shot and killed while hiding in a barn.

Old Main Streets

Enjoy this leisurely journey through “Small Town USA.” This 111-mile roundtrip travels from the town of Emmitsburg to Mount Airy and Thurmont and then to Westminster in Carroll County. “This byway serves up a heaping helping of small-town hospitality.”

Harriet Tubman Underground Railroad

From this 125-mile journey from Dorchester County’s Cambridge to Goldsboro in Caroline County, you can trace the secret network of trails, waterways and safe houses used by enslaved people to flee to freedom in the north before and during the Civil War. You’ll start out at the Harriet Tubman Underground Railroad Visitor Center in Cambridge and wind up in the historic towns of Greensboro and Goldsboro before reaching the Mason-Dixon Line along the Delaware border.

The Harriet Tubman Museum and Education Center
The Harriet Tubman Museum and Education Center in Cambridge.
(Photo courtesy of the Maryland Office of Tourism)

Religious Freedom

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Maryland — and in particular Southern Maryland — is the cradle of religious freedom in the United States. Why not travel the 189 miles — from Charles County’s Port Tobacco to Point Lookout, the most southern point on Maryland’s Western Shore — to learn about the state’s unique place in sectarian liberty? Among the stops is historic St. Mary’s City, known as the “birthplace of religious tolerance in North America.” St. Mary’s was the fourth permanent settlement in America and the site of the first Catholic chapel.

Chesapeake & Ohio Canal

Nicknamed “the Grand Old Ditch,” the C&O Canal is a marvel of 19th-century engineering that today is a popular hub with more than 200 miles of hiking, biking, bird watching and heaping portions of history. You’ll begin your journey at the Chesapeake & Ohio Canal National Historical Park’s Georgetown Visitor Center in D.C., pass through such towns as Hancock and Sharpsburg, and wind up in Cumberland. Along the way, you’ll find a plethora of mills, railway tunnels, waterfalls, parks, museums and visitor centers. 

For more information, go to visitmaryland.org.

O Say Have You Seen Maryland
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