Hidden In Maryland's Mountains Is An Artistic City With A World-Class Bike Trail, Scenic Byways, And Shops

Mention Maryland, and Baltimore and seafood likely come to mind. However, the Old Line State has a secret hideaway full of art, bicycle trails, charming shops, and some of the best mountain views around. The small city of Cumberland is about as far away from Assateague Island, which boasts pretty beaches, dunes, and forests, as you can get within the state lines. It's closer to Pittsburgh than Baltimore and nestled in Allegany County, giving you a different perspective of the state that is "America in Miniature."

Although Native Americans have inhabited this area along the Potomac River for millennia, Cumberland was founded in 1787, and became a major transit and manufacturing hub as the country bloomed. The city's rich history and historic infrastructure make it a great base for exploring the region by car, bike, or rail.

Cumberland is easy to reach on Interstate 68 and U.S. Route 220, on the north side of the Maryland-West Virginia border. From the Washington, D.C. area, Cumberland is approximately two and a half hours away, making it an easy weekend getaway. If you'd prefer not to drive, AMTRAK's Floridian stops in Cumberland on the way to Pittsburgh and Chicago every afternoon. Bring your bike on the train, but be sure to reserve space for it early. If you're visiting from further out, Cumberland does have a small airport on the West Virginia side, however, there are no commercial flights.

Cumberland's roots as a railroad hub laid the groundwork for some of the best biking trails and byways on the East Coast. Former rail lines and canals that served as gateways to the West or shipping routes have been converted to hundreds of miles of pavement for bicyclists, walkers, or outdoor enthusiasts, making it possible to travel to and from Washington, D.C. by bike.

The town is home to the Chesapeake & Ohio Canal – West Scenic Byway, running between Cumberland and D.C. During the Civil War, the canal divided the Union and Confederacy, and served as a key part of the underground railroad. Today, walk or bike over 184 miles of road to get a sense of the past and burn some calories. If you've got more than a few more miles in you, the canal connects in Cumberland with the 150-mile Great Allegheny Passage. Both trails have places to rest and relax on your journey, including campgrounds, hotels, and nearby watering holes to raise a glass.

If you're looking to literally start from 0, the National Road, America's first federally funded road, began in Cumberland back in 1811. This route laid the groundwork for Western expansion across Appalachia to the Midwest and beyond, and is currently part of U.S. 40, running from Atlantic City to San Francisco. In Cumberland, be sure to stop by the National Road Zero Mile Marker & Monument. If you're not sure about your itinerary on the route, use AI to plan the road trip of your dreams.

Cumberland's coming of age in the 1800s left a treasure trove of world-class and industrial architecture that has been repurposed for tourism throughout the city. Baltimore Street downtown boasts a pedestrian-friendly outdoor mall, museums, and restaurants in its burgeoning arts and entertainment district. Downtown has transformed from hosting major department stores in past decades to becoming a local business hub. You can find anything from electronics to quilts to antiques in the city's cute boutiques.  

Downtown is also home to Cumberland's Allegany Arts Council, a local nonprofit that supports and showcases the works of local talent in music, fine art, and film. While you're in town, visit one of the many free exhibitions. Just next door, Loft 129 is a local music venue and concert hall hosting special events and concerts across multiple genres, from rock to blues to country. Stop by, grab a drink, and see a local artist before they go mainstream in an intimate setting that's perfect for a night out.

While you're there, don't miss a Saturday evening witnessing the glory of Maryland's mountains on a historic and unique train ride. The Western Maryland Scenic Railroad departs from Cumberland. During select weekends throughout the year, unleash your inner Sherlock Holmes as you participate in a murder mystery event, complete with live actors and a full three-course meal. Guests for this event must be at least 21 years old, but families are welcome on other trains.