48 Hours in Cumberland

Legs outstretched to reach the pedals, I’m coasting along the tracks of the  Western Maryland Scenic Railroad on a rail bike—a pedal-powered vehicle designed for riding train tracks. I glide down a mountain, past stands of verdant trees dappled below with wildflowers, and, in the distance, the former ironworks village of Mount Savage. (Don’t worry, the train isn’t currently running.)

My fellow passengers and I feel a whoosh of cold air as we enter Brush Tunnel. Soon, we inhale the scent of honeysuckle and sassafras as we pass through a section of the ride that our guide has dubbed “Fruit Loop Forest” because of its intermingled fragrances.

We wave to a few bicyclists riding along the Great Allegheny Passage, a 150-mile rail trail that stretches from Pittsburgh to Cumberland, where it connects with the 184.5-mile C&O Canal Trail to form a continuous route to Georgetown in DC. An estimated 300,000-plus cyclists begin, end, or pass through Cumberland on their marathon rides along these trails. But as I’m already learning on my first morning in this area of western Maryland, called “The Mountain Side of Maryland,” there’s more than just bike trails to entertain a visitor.

Day 1

Get up early and energize yourself for the day with your choice of caffeinated beverage and a breakfast sandwich, such as the Reuben or classic breakfast burrito, at Café Mark in downtown Cumberland.

Next, drive to nearby Frostburg to begin your four-hour roundtrip rail bike and scenic train ride aboard the historic Western Maryland Scenic Railroad with Tracks and Yaks, the company that offers this unique experience. You’ll need to be at the Frostburg Depot at least 20 minutes before your 9 a.m. ride, but I recommend arriving even earlier to visit the moving Coal Miners’ Memorial in the small park next to the train station. It shares the stories of the many miners, some as young as 14, who lost their lives performing this dangerous work.

The rail-bike excursion requires very little exertion until the last mile or so approaching Cumberland, when you’ll need to pedal along flat ground. After a short layover, you’ll hop aboard the beloved Frostburg Flyer for the scenic train ride back to Frostburg. The train includes a dining car and several coach cars, which, if you’re lucky, will be pulled that day by Engine 1309—one of the nation’s oldest operating vintage steam locomotives. (You may want to opt for lunch on board, though it is pricey. Alternatively, bring a sandwich along.)

After returning to Cumberland, head to the Washington Street Historic District for a guided tour of Emmanuel Episcopal Church, built atop the site of 1755’s Fort Cumberland, considered one of the largest British military installations in North America at the time. You’ll see a model of the fort and visit the remains of the old earthworks below ground, which local lore suggests were part of the Underground Railroad network used to hide escaping enslaved people. Request a tour on the church’s website at least three days in advance; donations are appreciated.

Afterward, walk a short distance to the C. William Gilchrist Museum of the Arts (also called the Gilchrist Gallery & Museum). Housed in a restored early 19th-century Federal-style mansion, it features six bright galleries and a changing collection of art exhibits, often by local artists. Admission is free.

Wind down the afternoon with a microbrew at Dig Deep Brewing Co. or a glass of wine at Charis Winery & Distillery, both located at Canal Place, where the C&O Canal and Great Allegheny Passage meet. Treat yourself to an Italian dinner at Ristorante Ottaviani, just a short walk from Baltimore Street, Cumberland’s main drag.

When it’s time to turn in for the night, you have several choices for lodging, including the following:

• Fairfield Inn & Suites by Marriott Cumberland – Located adjacent to Canal Place, this hotel is a popular choice with cyclists.
• Rocky Gap Casino, Resort & Golf – This AAA Four Diamond resort in Flintstone is about a 15-minute drive from Cumberland. Set on scenic Lake Habeeb, it features three restaurants, an indoor pool and hot tub, a spa, and an 18-hole golf course.
• The Wills Hotel – Expected to open the winter of 2025/2026 on Baltimore Street, this 20-room boutique hotel is one of the most anticipated additions to downtown. It’s housed in a restored Italianate-style building with a rich history.

Day 2

If you’ve stayed at Rocky Gap Resort, which is located within the scenic expanse of Rocky Gap State Park, step out this morning into a playground of outdoor possibilities. A popular choice is hiking the 5.3-mile Lakeside Loop Trail that encircles Lake Habeeb. I took an abbreviated route that met up with the Canyon Overlook Trail and was rewarded with a view of a forested 1-mile-long gorge. This being summer, I could only imagine how exquisite the scenery would be in the fall. Have lunch at the resort’s Lakeside Grille, and then head back to Cumberland for the afternoon.

If you stayed downtown, rent a bike for a few hours from Wheelzup Adventures at Canal Place, and enjoy a morning ride on one of the area’s bike trails. Afterward, have a sandwich at European Desserts and More. As the name implies, you’ll probably be tempted with something sweet, too.

Stroll over to the free Allegany Museum, housed in a stately 1930s Neo-Classical Revival building in the heart of downtown. Inside, two floors of exhibits explore the history of Allegany County. On the main floor, browse a transportation exhibit that covers the area's pivotal role in early American travel, including the National Road (Route 40), the first federally funded highway, which began in Cumberland. The display also highlights the region’s importance as a transportation hub, with sections devoted to the C&O Canal and the railroad, both of which helped shape the city’s development.

Next, take a pleasant ramble along the recently revitalized Baltimore Street, where a smattering of independent shops and galleries line several blocks. Pop into Fort Cumberland Emporium for antiques and collectibles, or browse Madison Paige Boutique for women’s clothing and accessories. Don’t miss The Arcadian Gallery, an art space that also houses a sophisticated wine bar. It’s run by former National Geographic art director Chris Sloane, who has a keen eye for the nature-themed original art, limited editions, and prints that adorn the gallery walls.

D’Atri Pasta & Subs is a solid choice for a filling, budget-friendly dinner. The quick-service restaurant is best-known for its cheesesteak, but you’ll also find a wide selection of hot and cold subs, salads, and pasta dishes. For dessert, head next door to Queen City Scoop Shop for a generous serving of frozen custard.

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Cumberland earned the nickname “Queen City” back in the 1800s, when it was second only to Baltimore as a hub of industry, transportation, and culture in the state. Today, its greatest draws are its outdoor adventures, historic charm, and warm-hearted locals who never let you forget how welcome you are here.