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America’s First Road Trip

America’s First Road Trip


Be a pioneer as you follow America’s oldest highway to discover important parts of early American history and outdoor adventure.


Start: Allegany Museum

Finish: Town Hill Bed and Breakfast and Overlook

Distance: 2 days, 5 stops, 44.6 miles



Allegany Museum & Mile Marker “0”

3 Pershing St, Cumberland, MD 21502

Begin America’s First Road Trip with a visit to the Allegany Museum, Allegany County’s first-class museum presenting the cultural, geographic, and commercial history of Appalachian Maryland, West Virginia, and Pennsylvania. Be sure to check out the soon-to-open “Crossroads of America” exhibit, which tells the story of how Allegany County developed through its location as one of the only few routes to connect Georgetown and the east coast to the westward expansion. Just a short walk from the museum is the National Road Monument, which marks Mile “0,” or the beginning of the National Road.




LaVale Toll Gate House

National Hwy, LaVale, MD 21502

Establishing mile marker “1,” the LaVale Toll Gate House was the first structure erected along the National Road and is the last standing toll gate in Maryland. Interpretive signage indicates fees for wagons, animals, and pedestrians to use the road and you can peer into the historic structure for a look into the past.




Frostburg Main Street

Main Street, Frostburg, MD 21532

A state-designated arts and entertainment and Main Street district, Frostburg owes its humble beginnings to the construction of the National Road, which runs right through the heart of downtown. Stop to see the Braddock Stone, one of America’s oldest road signs which dates back to the mid-1700s when General Braddock marched through Western Maryland. Or, pop into the Hotel Gunter to visit Toasted Goat Winery, once a popular resting place along the National Road, to see their old speakeasy and cock-fighting ring (which is no longer in use). While you’re there, check out the Route 40 Brewing and Distilling Company.




Great Allegheny Passage

13 Canal St, Cumberland, MD 21502

Outfit yourself with a bike rental or bring your own to experience the internationally recognized, 150-mile rail-trail that runs from Cumberland, MD to Pittsburgh, PA. The Great Allegheny Passage winds its way through Mountain Maryland’s Allegheny Mountain range and runs adjacent to the Western Maryland Railway, which is now home to the Western Maryland Scenic Railroad.




Town Hill Overlook and Bed and Breakfast

31101 National Pike NE, Little Orleans, MD 21766

Take a scenic drive through Mountain Maryland’s countryside that ends with quite a view at Town Hill Overlook. Enjoy the extensive views of the eastern slopes of Green Ridge State Forest, and in the Spring and Fall migration season, this is a popular site to spot golden eagles. Pop across the street to Town Hill Bed and Breakfast, which was the first tourist hotel in the state to accommodate the automobile traveler, due to its convenient location along the National Road.


About the Author

Allegany County Tourism

Allegany County Tourism is the destination marketing office ​​for Allegany County, Maryland. For more information on road tripping to Allegany County, Maryland visit:

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