A trail for every traveler
Whether you want to get outside, explore local eateries or dive into history, Allegany County, the Mountain Side of Maryland, has it all.
By WP Creative Group

This summer, all signs point to happier trails. And good news: there’s a bounty of them to explore — on foot, on wheels or by kayak — in Allegany County, a northwestern Maryland destination prized for its outdoor recreational activities, historic sites and local cuisine.
“Our trail systems are so popular because they offer a hybrid experience where you are able to connect with nature and be outdoors, but then you come upon towns where you can go into the community, expose yourself to the history of the region and enjoy food and beverage,” says Ashli Workman, Director of Tourism, Allegany County Government. “You get a small taste for everything, depending on the length of time you’re with us and what’s driving your experience. Are you coming for the outdoors? Are you coming for food? Are you coming for history? We’ve got a trail for that.”
Here, learn more about Allegany County’s trails for every kind of traveler.
Grab your bike, your kayak, your backpack — or all three
With over 70,000 acres of public land, 200 miles of trail systems and Maryland’s largest contiguous state forest, Allegany County has plenty of outdoor adventure on tap. Mandela Echufu, Chief Adventure Officer and Owner of Wheelzup Adventures, recalls falling head-over-heels for the area’s wild beauty while passing through on his commute — so much so that he ultimately left behind his medical career in Pittsburgh to begin a whole new life. “There’s this place called Sideling Hill, and the fall colors were so amazing that I literally pulled over for about 20 minutes. I said to myself, ‘I’m going to start checking this stuff out.’ I started hiking a little bit. I started biking and road riding. I became a ski patroller and led tours and started the shuttle business and opened the shop. I found myself. This place chose me. I’ve been here for the past 16 years now.”

Echufu, like so many who visit for the first time, learned that — thanks to a low population density — you can discover a piece of paradise for yourself in Allegany County. Even more well-known hiking and biking trails, such as the Great Allegheny Passage and the C&O Canal Towpath, feel relatively untouched. More into watersports? Echufu recommends stopping by the Potomac River. Meanwhile, road cyclists can ride in peace without constantly looking over their shoulder for oncoming cars on routes like Mt. Savage Loop.
Because of the proximity of these breathtaking sites — many of which are a 15 to 45-minute drive apart — it’s simple to plan an action-packed day of world class paddling, biking and hiking. Even skiers are in luck. “Another thing that sets us apart is the elevation changes. In Cumberland during the spring, you can bike one day and drive for 40 minutes and go skiing or fishing in New Germany State Park. The microclimates that exist in our community make multi-sport, multi-adventure days very easy,” Echufu adds.
Follow your tastebuds
Working up an appetite? Allegany County has a trail for that, too. Boasting the very best of the area’s hyperlocal food and drink, dedicated food trails show travelers where to fuel up with a morning jolt of coffee, seasonal beer and decadent treats while exploring outdoors or cruising along open roads. Enthusiastic gourmands can even spend their entire trip following the Donut & Coffee Trail, tracking down homespun custard on the Ice Cream Trail and visiting the area’s award-winning wineries, breweries and distilleries on the Mountain Maryland Tap & Pour Tour. Many of these, such as Dig Deep Brewing Co., emphasize a strong connection to their community that’s revitalizing the county.

“Dig Deep Brewing Co. is the first production brewery in Cumberland in 45 years. It’s very important for us to honor the tradition of excellent brewing and to be a working person’s pub where no matter your differences, you can get together and have a drink and hang out,” says Lydia Savramis, part of the Dig Deep Brewing Co. team. Visible from the C&O Canal trail, Dig Deep Brewing Co. proves a popular spot to stop for a Side Chick blonde lager — their best-selling beer — and kick back while listening to local musicians. The brewery even collaborates with another beloved Cumberland institution, Basecamp Coffee Company, by using concentrated cold brew to make their Appalachian Trail porter. Many Allegany County businesses are bonded in another way: a passion for quality and connection to the past.

“It comes back to the Appalachian tradition of using your hands to make something,” says Workman. “We have all these historic, made-in-Allegany County businesses that have been around for generations like McFarland Candies and Caporale’s Bakery, where you can pick up fresh croissants and donuts. Meanwhile, The Toasted Goat Winery operates tastings at Hotel Gunter, which was a true speakeasy during the Prohibition era.”
Soak up the past
History-lovers won’t just find the past tucked away in basements. You can uncover 300 years of American heritage throughout the many trails, streets and scenic byways of Mountain Maryland.
Take your time following America’s oldest road, stopping along the way for a trip on the Western Maryland Scenic Railroad, an outing that allows travelers to experience living history in a first-class vintage train powered by a diesel or steam locomotive. During the 4.5-hour round trip, passengers start and end in downtown Cumberland with a 90-minute layover in Frostburg, allowing time to explore the charming town’s quaint shops and restaurants, like Princess Restaurant, which famously served President Harry S. Truman.

President Truman isn’t the only Commander in Chief to have a connection to Allegany County. George Washington ventured there on his first diplomatic mission at the beginning of the French and Indian War. Today, visitors can retrace his steps on the George Washington 1753 Trail, including at Emmanuel Episcopal Church, a 19th-century building set on the site on Fort Cumberland. The fort’s tunnels — which were originally used for storage and as an escape route for soldiers — served another purpose nearly 100 years later as part of the Underground Railroad. There, escaped slaves hid for hours or even days before braving a four-mile hike to freedom across the Mason-Dixon line in neighboring Pennsylvania. Tours are offered throughout the year, yet it remains one of the area’s many extraordinary, lesser-known highlights.
“If I had a dollar for everybody who comes from Annapolis or Baltimore or D.C. and says, ‘Wow, this place is a hidden gem,’ I’d be pretty rich by now,” Echufu jokes. “If you come to be a tourist, there’s nothing wrong with that. But, Allegany County is the place for those looking to reconnect, rejuvenate and just have pure, good fun.”
Maryland. Be Open.
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