Whatever your idea of adventure, you’re likely to find it in Allegany County, “the Mountain Side of Maryland.” With an abundance of outdoor recreational activities, historic sites, and award-winning wineries, breweries, distilleries, and eateries, you’ll find a trail for just about any age or interest in this picturesque part of the state. Here are just a few of the spring and summer trail experiences Allegany County has to offer.

Great Allegheny Passage

Connecting Pittsburgh, PA, to Cumberland, MD, the Great Allegheny Passage (GAP) trail offers 150 miles of scenic rail-trail for biking and hiking, with majestic views of Maryland’s mountains. The trail follows the route of the historic Western Maryland Scenic Railroad, and it’s the only location along trail where bikers can ride through a tunnel at the same time as a passing train. The GAP trail links up to the C&O Canal Towpath in Cumberland.

The official trail towns of Frostburg and Cumberland boast Main Street districts full of unique and charming shops, restaurants, and arts and entertainment venues. Be sure to take the self-guided walking tours to admire the architectural beauty and enduring history when you visit.

C&O Canal Towpath

The 12-foot wide, nearly level path was built for mules to pull the canal boats along the 184.5-mile canal from Cumberland, MD, to Georgetown in Washington, D.C. Today, the path is maintained by the National Park Service and draws visitors from all over the world looking for scenic biking and hiking.

Tracks and Yaks

If you’re looking for something fun and different for all ages, try rail biking! Pedal-powered tandem or quad rail bikes take riders along the smooth, steel railroad tracks. This is not a physically strenuous activity since the tracks steer the rail bikes and the terrain is mostly downhill. The Track and Yak excursion includes a 15-mile rail bike trip, a 4-mile float on the North Branch of the Potomac River in a kayak or tube, and a shuttle bus back to Frostburg Depot. Shorter rail bike-only tours are also available.

Ice Cream Trail

If your warm weather goals are to sample as many sweet frozen treats as possible, the Ice Cream Trail is for you. From end-to-end, the self-guided drive is just under 55 miles and includes nine stops at local eateries. Or, you can take a break from biking or hiking one of the trails above to pop into one or two of them, such as the Oak Barrel Café, offering soft serve and smoothies, or Frostburg Freeze, family owned and operated for over 50 years, purveyors of the Boston Shake—a hot fudge sundae inside a milkshake or a milkshake poured over a hot fudge sundae, depending on your viewpoint.

Mountain Maryland Tap and Pour Tour

If your idea of a treat leans more toward adult beverages, this is your kind of tour. Mountain Maryland’s Tap and Pour Tour was recently named “Best Beer/Wine/Spirits Trail” by Blue Ridge Outdoors magazine. Visit the area’s award-winning wineries, breweries, and distilleries, including 1812 Brewery, the first farm brewery in Allegany County, located on 190 acres where they grow their own hops, and Charis Winery and Distillery, offering award-winning sweet and semi-sweet wines and brandy, as well as seven different oils and balsamic vinegar for sampling.

For even more ideas, destinations, and events, visit our website where you can request a destination guide.

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Do you crave fresh air and stunning fall foliage? You’ve got to check out the Great Allegheny Passage. Named one of the ‘Top Fall Trips in the World’ by National Geographic, the trail starts in Cumberland and follows the route of the historic Western Maryland Railway up toward the Eastern Continental Divide. The 150 mile trail winds through Maryland’s mountains to connect with Pittsburgh, Pennsylvania, and travelers can catch majestic views across four states from the overlook outside the Big Savage Tunnel just over the Mason & Dixon Line. Grab your backpack, your bike, or even your skis when the snow begins to fall and get going – you won’t want to miss this.

If outdoor sports aren’t your thing, no worries – Mountain Maryland has trails for you too. Climb aboard the Western Maryland Scenic Railroad for a range of experiences on the rails, with astounding views, authentic coaches, and fun for the whole family. Or try Tracks and Yaks, Maryland’s only rail biking excursion, which will whisk you through lush hills and valleys on tandem or quad railbikes. If you’re more comfortable in the car, drive the three-hour, 45-mile, self-guided scenic overlooks tour of Green Ridge State Forest. Maryland’s largest contiguous forest is not so green this time of year, and you’ll be mesmerized by the tapestry of fall colors.

While losing yourself in Mountain Maryland’s natural splendor, take a tour through history along the C&O Canal Towpath. One of the most-visited National Parks in the U.S. last year, the nearly 200-mile canal connects the region’s towns, parks, and forests, as well as the Potomac River. Learn about local industry, transportation, and recreation dating back to the early 1800s at the Allegany Museum and Canal Place Heritage Park. Then take it for yourself — the 12-foot wide, nearly-level towpath is perfect for biking and hiking. Stop for self-guided tours of Cumberland and Frostburg, which will walk you through the history and culture of these charming trail towns.

Before, after, or amid your outdoor exploits, reward yourself with delicious treats along Mountain Maryland’s tastier trails. The Tap and Pour Tour was named ‘Best Beer/Wine/Spirits Trail’ in Blue Ridge Outdoors Magazine’s 2021 ‘Best Of’ awards. Bask in the ambiance of outdoor gardens and patios at award-winning wineries, breweries, and distilleries, or take your favorites in a growler to go. For early birds, the irresistible offerings along the Donut and Coffee Trail will give you the sugar rush and caffeine buzz needed to knock out an early climb or a day of kayaking.

There’s something in the autumn air, something that drives us to get our, explore, and chase down adventure. Lots of places have incredible fall experiences. But if you’re looking to pursue your passions against a backdrop of sweeping mountain views and vibrant fall foliage, there’s only one place to go: Mountain Maryland.

Visit mdmountainside.com/startshere to learn more and request a destination guide.

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Started by the Grammy-winning, York, PA-born Del McCoury eight years ago, DelFest offers some of the best bluegrass in the country each year, including Old Crow Medicine Show, Trampled by Turtles, Railroad Earth, and Jason Isbell this Memorial Day weekend. (Jason Isbell and his wife Amanda Shires’ recent performance on The Late Show was one of the highlights of David Letterman’s closing run of musical guests.)

But spread over four days and nights—and late nights—music starts Thursday afternoon and goes to 3:30 a.m. Friday, Saturday, and Sunday, the 8th annual DelFest in Cumberland also offers a rare chance to mix Western Maryland camping, hiking and biking with music.

Sitting along the Potomac River at the base of the Appalachian Mountains, Cumberland was once an important railroad and canal junction and western gateway. Today, at the nexus of two of the top bicycling trails in the eastern U.S.—the C&O Canal, which begins in D.C., and the Great Allegheny Passage, which runs to Pittsburgh—downtown Cumberland has experienced a rebirth of sorts as a bicycling and recreational sports hub.

Stringing the two trails together, bicyclists literally come through Cumberland from all over the world today to ride from the Nation’s Capital to the Steel City (or vice versa) on 330 connected, car-free miles, either camping or staying in small town lodging and B&B’s along the way.

At DelFest, hosted at Cumberland’s Allegany County Fairgrounds, all multi-day passes include on-site, walk-in camping with RV hookups also available. The family friendly environment includes activities for kids, including, of course, biking or hiking on either one of the two trails.

There are a ton of bike shops situated on or near the two trails, including the Cumberland Trail Connection, which is seated right where the two trails come together downtown. Most shops rent bikes and provide shuttle service, if necessary. Many of the lodging facilities, including Cumberland’s The Inn on Decatur and Frostburg’s Trail Inn, offer bike and hike-friendly services as well.

We’re going to be doing some biking and camping ourselves this weekend in Cumberland, looking forward not just to the scenic mountain air—the weather looks great, by the way—but DelFest’s great music, too.

We should probably note that the local legends and festival namesake, the Del McCoury Band, won a “Best Bluegrass Album” Grammy in 2014 for their work, The Streets of Baltimore.

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Amtrak said it will soon begin to introduce the new, bicycle rack-equipped baggage cars on all of its long-distance trains, and that during upcoming field testing, “the baggage cars will travel to Chicago, New Orleans, Miami and along the Northeast Corridor to undergo testing for speed, stability, braking and baggage handling.”

“It’s clear that Americans want a national system of intercity passenger rail and Amtrak is moving ahead to build new equipment to meet customer demand,” said Amtrak president and CEO Joe Boardman in a recent Amtrak blog post.

By the end of 2014, Amtrak said, the new baggage cars and luggage racks for unboxed bikes will be used on all 15 long-distance routes, including the Capitol Limited, which runs between Washington, D.C. and Pittsburgh. The bonus of that route is that is closely tracks the linked C&O Towpath and Great Allegheny Passage — a popular, 330-mile, uninterrupted, off-road, bicycle/walking trail that extends from the D.C. through Harper’s Ferry, Cumberland, and Frostburg — all the way to the Iron City. 

(On a personal note, I did this ride last fall, which was fantastic, but without easy train availability I had to work around another friend’s planned vacation to Pittsburgh, in order to hitch a ride home.)

“It’s great to have Amtrak understanding how important the bike tourism industry is,” Linda Boxx, board member of the Allegheny Trail Alliance, who has worked for years to persuade Amtrak to provide better accommodations for bikes, told the Pittsburgh Post-Gazette.

Currently, Amtrak offers roll-on service only a few routes, and for now, those who took their bikes on the Capitol Limited were required to box them as checked baggage, which of course, required disassembly and assembly. And riders, as it has stood, could not disembark anywhere but Pittsburgh and Washington, because in-between station stops aren’t staffed with baggage handlers.

Last October, Amtrak invited 20 cyclists to take their bikes on the Pittsburgh to D.C. Capitol Limited train in a successful one-day trial of roll-on/roll-off service.

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