Frederick to Hagerstown
Including MD 144 & US 40 Alt
Recognized as one of America’s most distinctive destinations, downtown Frederick is the hub from which charming Main Street communities, romantic accommodations and inspirational attractions fan out like the spokes of a wagon wheel. Two centuries of architecture are represented at numerous homes and public buildings, including the Barbara Fritchie House and the National Museum of Civil War Medicine. The town also features entertainment ranging from dinner theater productions to minor-league baseball. At the end of a long day, one of Frederick’s inns or bed and breakfasts is a welcome sight.
As you head out beyond Braddock Heights and the farming village of Middletown, consider making time for a sidetrack into Washington Monument State Park, site of the first monument erected in George Washington’s honor. The park is also located along a noted migratory bird flyway, so bring your binoculars.
Continuing west, the farmland of Funkstown is dotted with Pennsylvania-Dutch bank barns and smaller English-style structures.
Hagerstown to Cumberland
Including US 40, I-68, I-70 & MD 144
So many early railroad companies were linked into Hagerstown that it earned the nickname “Hub City.” The C&O Canal also flowed through this area, which now draws legions of bicyclists and hikers. The town itself — featuring the South Prospect Street Historic District — has a roundhouse museum among several other sites dedicated to preserving local history.
Traveling along US 40, look for the small waterfront park that offers a fine view of the five stone arches that support the 210-foot-long Wilson Bridge. Dating back to 1819, it’s the oldest and longest bridge of its kind in Washington County. Passing through Clear Spring, site of the 160-year-old Wilson Country School and Store, you can sidetrack south along MD 56 to Fort Frederick State Park. Based in Big Pool, the fort was the cornerstone of Maryland’s defense more than 250 years ago during the French & Indian War.
Next in line is Hancock, where a national historic park offers a deeper exploration of canal life. After a climb up Sideling Hill, which was the scene of many stagecoach mishaps due to the steep turns, you’re ready for a relaxing round of golf amid the ridges and valleys of Rocky Gap Lodge, Spa & Golf Course, followed by a satisfying stay there or in Cumberland.
Cumberland to State Line
Including US 40 Scenic, I-68, US 40 & US 40 Alt
Cumberland, like Hagerstown, was a transportation crossroads with ties to highway, railroad and canal transportation, and is now just as popular for its galleries, theaters and museums.
A steam-engine train ride on the Western Maryland Scenic Railroad or an exhilarating bike ride on the Great Allegheny Passage rail trail takes you to Frostburg, site of a nationally known carriage museum.
In LaVale, the route passes Maryland’s only remaining National Road toll gate house, outside of which a plaque still displays the cost for wagons, animals and pedestrians to pass.
Conestoga wagons once crossed the Casselman River Bridge, a single-span, stone-arch structure built for the National Road near Grantsville in 1813. Access to the bridge is available from a former stagecoach stop that is now known as the Spruce Forest Artisan Village and serves as a cultural center promoting local arts, crafts and music. US 40 Alternate then winds through the northern section of Savage River State Forest and over Keysers Ridge to the Mason-Dixon Line.