Step back in time and experience America’s first great road trip along the Historic National Road, starting right here in Allegany County, the Mountain Side of Maryland. This legendary route, born in 1806 under the vision of President Thomas Jefferson, became the nation’s first federally funded highway, stretching from Cumberland, MD, to St. Louis, MO, and laid the foundation for today’s U.S. highway system.
Travelers today can follow in the footsteps of pioneers along this 45-mile scenic byway, discovering historic landmarks, vibrant mountain towns, and outdoor adventures that showcase the best of Mountain Maryland.
Day One: History Comes Alive on the National Road
Mile Marker “0” – National Road Monument, Cumberland
Your journey begins at Riverside Park in Canal Place Heritage Park, where a monument marks Mile “0” of the Historic National Road. Nearby, visit George Washington’s Cabin, a log structure once used by Washington himself during his time in Cumberland.
Allegany Museum – Crossroads of America Exhibit
Step inside the Allegany Museum to explore how our county became a gateway to westward expansion. The “Crossroads of America” exhibit highlights Allegany County’s role as a vital link between the east coast and the frontier.
LaVale Toll Gate House – Mile Marker “1”
Just west of Cumberland, stop at the LaVale Toll Gate House, the first structure built along the National Road and the last surviving toll house in Maryland. Interpretive signs reveal what early travelers once paid to cross.
Frostburg Main Street
Follow the National Road into Frostburg, a state-designated Arts & Entertainment District and Maryland Main Street community. Stroll through local shops, stop to see the Braddock Stone at the Frostburg Museum, one of America’s oldest road markers, or step inside the Hotel Gunter, which once welcomed travelers—and even housed prisoners—along the National Road. During Prohibition, the hotel operated a speakeasy in its basement, where you can still view the original space and old jail cells today.
Day Two: Outdoor Adventure Meets Roadside Flavor
Great Allegheny Passage
Swap four wheels for two as you ride a section of the Great Allegheny Passage (GAP), a world-class rail-trail stretching 150 miles from Cumberland, MD, to Pittsburgh, PA. Bring your bike or rent one downtown to experience sweeping mountain views and connections to the C&O Canal Towpath.
Puccini Restaurant
Refuel at Puccini Restaurant, famous for its wood-fired pizzas and warm hospitality. Located in the historic 1818 Hinkle House, the restaurant once served as a Civil War hospital. Ask for a peek at the attic etchings left behind by soldiers.
Rocky Gap State Park
Spend the afternoon immersed in nature at Rocky Gap State Park. Hike the Canyon Overlook Trail for big views with little effort, or take on the 5-mile Lakeside Loop Trail around shimmering Lake Habeeb. Paddle, fish, or simply unwind in over 3,000 acres of Mountain Maryland beauty.
Town Hill Overlook & Bed and Breakfast
End your journey with a breathtaking view at Town Hill Overlook, a favorite spot for birdwatching during migration season. Across the road, step inside Town Hill Bed and Breakfast, the state’s first auto-traveler hotel, welcoming guests since the dawn of the automobile age.
Plan Your Road Trip to Mountain Maryland
Whether you’re a history buff, outdoor enthusiast, or foodie, Allegany County offers the perfect blend of heritage and adventure. From mile marker “0” of the Historic National Road to scenic overlooks, charming small towns, and trails that stretch for miles, you’ll find that America’s first road trip is still one of its best.
