How to Get the Most Out of Cumberland, Maryland

BRONZE STATUE A BOY AND HIS MULE IN CANAL PLACE NEAR THE WESTERN MARYLAND SCENIC RAILROAD STATION, COMMEMORATING THE HARDWORKING MULES THAT PULLED CANAL BOATS ON THE C&O CANAL. | PHOTO BY SEAN COLLIER

Cumberland is a place where people go to get outside. Its position at the end of the Great Allegheny Passage hiking and biking trail — and the spot where that trail meets the C&O Canal Towpath, continuing on to Washington, D.C. — has made it a regular stop for outdoor travelers and anyone looking to rest while enjoying the beauty of Maryland’s mountain region.

The complete Great Allegheny Passage is a relatively recent achievement; the trail connecting Pittsburgh and Cumberland was fully completed in 2013. Cumberland, however, has been a waypoint for travelers for millennia. A visit to the charming Allegany Museum details how Indigenous tribes used this area as a relatively easy path through the mountains long before the arrival of Europeans in North America. Centuries later, Fort Cumberland was at one point the westernmost outpost of the British during the French and Indian War; even later, Cumberland became the starting point of the National Road, the precursor to the modern Interstate system.

THE NATIONAL ROAD MARKER | PHOTO BY SEAN COLLIER

(By the way, that’s not a typo or quaint spelling on the name of the museum. Cumberland sits in Allegany County, Maryland; both names derive from Indigenous words, with variations based on locale.)

With that long tradition of rugged travel, it’s no surprise that Cumberland has become a landmark for modern bikers, hikers and campers. This is not merely a place for the great outdoors, though; it’s a place that embraces the outdoors in general. In front of nearly every building are parklets and benches; each restaurant has its own outdoor seating, where diners while away the hours during warm (or even temperate) months. Sit in one place for a few minutes, and you’ll notice groups of folks lingering — and calling out greetings to cyclists as they pass by.

This easygoing activity centers around the town’s historic Downtown area, a walkable and inviting collection of shops and restaurants. Clustered around Baltimore Street, the city center invites more exploration than its relatively small size would indicate. There are cafes, stores full of antiques and collectibles and cultural institutions — such as the 95-year-old Embassy Theatre and the impressive Ferleman Gallery — around every corner, including the whimsical Merchants Alley. Any visit should include an hour or two poking around new arrival Lily Books & Cafe, a combination coffeeshop and new and used bookstore, and a visit to The Rosenbaum, a former department store turned indoor shopping and dining district.

GEORGE WASHINGTON’S HEADQUARTERS IS A HISTORIC LOG CABIN TWICE OCCUPIED BY GEORGE WASHINGTON. | PHOTO BY SEAN COLLIER

Speaking of dining: Cumberland also is a place to refuel. Those who are looking to get their fill of carbs before a day on the trail — or anyone with a love of Italian-American cuisine — should make a reservation at Ristorante Ottaviani, a storefront restaurant as inviting as it is filling. Writing on one wall reads “a tavola, non s’invecchia” — Italian for “at the table, one never grows old.” Try a dish with the house signature Abruzzo sauce, a bold and cheesy topper that’s great on salmon — and, by all means, save room for cannoli. (For more worthy eateries, see “Where to Eat.”)

Cumberland also is a neighbor to one of the most understated yet relaxing resort casinos in the area: Ten minutes away, Rocky Gap Casino, Resort and Golf sits in nearby Flintstone, Maryland, just outside of Rocky Gap State Park — an unlikely but delightful collision of gaming and nature.

This is a resort with a secret weapon: breathtaking Lake Habeeb, a peaceful body of water nestled against a picturesque hillside. The 5-mile Lakeside Loop trail passes within feet of the resort and is the perfect antidote to a night of indoor fun — and it’s tough to conceive of a better hotel morning than waking up and heading to Rocky Gap’s Lakeside Grille. As you sip your coffee and gaze out at a remarkable, panoramic view of the lake and mountains, you’ll wonder if you could ever enjoy a sad continental breakfast ever again.

In warmer months, a faux beach invites guests to grab a drink from the outdoor bar and unwind by the water. Rocky Gap also offers live entertainment and a Jack Nicklaus Design golf course — and all these activities are enhanced by the striking scenery. There are plenty of casinos and hotels in the area, but none have such a memorable setting.

Whether you’re staying at Rocky Gap or in Cumberland itself — and whether you’re bound for Washington, D.C., or just looking to get an hour of exercise — you need to get out on the trail. At Wheelzup Adventures, you can rent bicycles and all the gear you’ll need to begin your journey, whether you’re planning a day trip or a quick jaunt. You have the option to be shuttled to a trailhead 25 miles from Cumberland and given careful instructions on biking back. (The route on that venture is all downhill, too.)

Even if such excursions aren’t your cup of tea, there’s plenty in and around Cumberland and Rocky Gap to fill your weekend — and endless opportunities to spend time in the open air. Whether your vision of the outdoors is conquering the Passage over multiple days or sipping a cocktail outside a casino, this mountainous, beautiful region will welcome you.

Where to Stay

If you’re not riding the Great Allegheny Passage, Rocky Gap is your best bet. If you are and want to stick closer to Cumberland, opt for Cumberland Inn & Spa, a 13-room hotel converted from a pair of 19th-century homes. The rooms are cozy, and separate bike storage is included.

Where to Eat

Go for the Catfish Pontchartrain or the Shrimp Creole at Baltimore Street Grill, which also offers a long list of burgers and pub grub along with its Louisiana flavors. Jambalaya is top-notch at The Crabby Pig, a casual spot adjacent to the C&O Canal Towpath Trail. Both spots have outdoor seating. In the morning, stop in at Café Mark for invigorating coffee blends — including seasonal-flavor flights — and great baked goods.

When to Go

Rocky Gap is a year-round destination. If you’re looking to get the most out of Cumberland, consider visiting during the Heritage Days celebration (usually held in September) or Fallfest (typically in October); check cumberlandalive.com for this year’s dates.