Biking: A Tale of Two Trails in Western Maryland

Spent Labor Day weekend in Cumberland, biking sections of the C&O Canal Tow Path and the Great Allegheny Passage. It was awesome! Below are pics and a few details about my trip, including restaurant, lodging, and bike rental recommendations.

Midway Between Pittsburgh and D.C.

Cumberland’s heyday was pre-WWII, but the city is working to reinvent itself as a regional tourist destination. Much of its history and appeal center on the Chesapeake & Ohio Canal and the Great Allegheny Passage.

The Canal

Construction began Independence Day 1828, but the entire DC-to-Cumberland route wasn’t finished until 1850. By then, railroads had taken over. The canal’s barges, which were pulled by mules over 184 mountainous miles and through 74 locks, couldn’t compete. Ingenious in design, industrious in its making, but nearly obsolete from the start, the canal was used to ship mostly coal and timber for 100 years or so. In the 1970s, it was made into a National Park.

When you bike the trail today, you bike on the path the mules used while pulling the barges. The locks are still there, in various states of disrepair. Many are full of still water, some of it black and malignant looking. But others are full of duck weed and turtles. Some are dry. Some old gates are still in place, as well as lock houses and plenty of signs explaining the history of the canal, park, and trail.

The GAP

The Great Allegheny Passage is a 150 mile rail trail from Pittsburgh to Cumberland. We started just north of the Eastern Continental Divide. It was raining, so it was fun to think about the fact that rain drops on one side were falling into the Gulf of Mexico watershed while raindrops on the other were falling into our beloved Chesapeake Bay watershed. Because the divide is the highest point of the trail, it was literally all downhill from there. The easiest, fastest, most beautiful miles I’ve ever biked.

There were three tunnels, which were neat. I’ve biked the NCR’s Howard Tunnel a few times, but these were longer and darker. Two had lights, although some of them were out. Still, no need for a headlamp or phone flashlight. We crossed the Mason-Dixon line, chuckling a bit about how much fanfare the trail gives this border crossing. (We live about 8 miles from it farther east and cross the line multiple times a day, nearly every day.)

Bone Cave, a few miles west of Cumberland, was creepy. I’m used to using “medieval” as an adjective for “old” or “ancient.” This cave made medieval seem as modern as an iMac. It was discovered in the early 1900s when the railroad was being built. Fossils and bones from 200,000 years ago have been found inside, including cave bears and saber-toothed cats. Rock fall and a fence blocks the entrance… but I had no intention of venturing in!

The Western Maryland Scenic Railroad is still in operation. You can ride from Cumberland to Frostburg and back — or take your bike on the train and ride the GAP back. We stopped to watch the train turn around on the turntable and left before it did, so we were able to lay pennies on the track to take home as souvenirs.

Where to Stay, Eat, and Drink; Who to Rent Bikes From

We stayed at the Inn on Decatur Street. The owner offers a nice package for bikers, which she calls the “Tale of Two Trails.” You get two nights, two hot breakfasts, packed lunch for the trail, and van support for two days of riding. Riders usually do a portion of the C&O Canal one day and the GAP the next.

(When I first booked the trip, I mistakenly told Craig the package was called “A Taste of Two Trails” and he thought there would be rest stops with wine and beer tastings. Ha! Not exactly…)

We went with another couple and had dinner Saturday night at Ristorante Ottaviani, which was lovely and charming. We ate in their outdoor patio area, which is an alley strung with white lights. They had live music, great food and wine, and a server who’s thinking about getting into beekeeping. It was fun chatting with her!

My friends rented bikes from the same people who provided our van support, the Cumberland Trail Connection. The shop also happens to have beer brewing experts on staff. Some of them work for Cumberland’s new craft beer place, Dig Deep Brewery, which is renovating the first floor of the historic Footer’s Dye Works Building. We swung by to see the space and taste a sample. Can’t wait to go back. Beer and biking – what could be better? 😉

Cumberland: Recommended for…

  • Bikers!
  • Outdoor enthusiasts
  • Fans of small mountain towns
  • Anyone interested in American history
  • Cat lovers! (Cats per capita, Cumberland rivals Rome and Istanbul!)

More information


For summer 2019, Jill’s goal was to bike 750 miles. During her Cumberland weekend, she biked nearly 50 miles, allowing her to blow past her goal and hit 772+ for the season. She mostly rides rail trails and has given talks at her local library and senior center on the history of Maryland’s Northern Central Railroad, its towns, and rail trail. One day, she’d love to bike from Pittsburgh to D.C.