Last Updated on July 7, 2023
What comes to mind when you think of Maryland–sailing, beaches, and crab cakes? I’m sure you answered yes, but turn west and you’ll find the verdant mountains of Allegany County, Maryland. Located within a two-hour drive of Pittsburgh, Washington D.C., and Baltimore, this year-round destination is laden with history, outdoor recreation, farm-to-table dining, and gaming.
The Maryland mountainside is ideal for a long weekend and then some.
Allegany County boasts numerous destinations recognized annually by the Best of the Blue Ridge Awards. Previous winning categories include the best winery, best biking trails, best music festival, and best ice cream to name a few. With so many choices, the possibilities are endless.
The Maryland mountains of Allegany County were a surprising discovery. It’s not only a great outdoor destination, but also a place rich in history. You’ll find fine dining, local delicacies, a vibrant arts community, and plenty of good memories.
Rocky Gap State Park

Sporting Lake Habeeb with the self-proclaimed bluest water in the state, Rocky Gap State Park offers over 3,000 acres to explore. On a sunny day, families gather at one of the park’s three beaches to enjoy wading in the crystal-clear water. Canoes, kayaks, and paddleboards are also available for rent at affordable rates.
Expansive picnic sites complete with charcoal grills provide for al fresco meals. Surrounded by plenty of green space for a pick-up soccer game, the facilities are well maintained with restrooms available at the visitor facility.
For those wanting to stretch their legs, there are over 15 miles of trails offering expansive mountain views and dense hemlock forests. A short quarter-mile walk along the Canyon Overlook Trail yields inspirational visions of a mile-long gorge. Near the trail parking, the paved handicap-accessible Touch of Nature Trail leads to the Lakeside Trail. Follow the 5.3-mile well-marked loop around Lake Habeeb and enjoy watching boaters and fishermen from the rocky coastline.
If you want to stay longer than a day, campsites are also available in the park. Additional information about this gem of a park can be found at: https://dnr.maryland.gov/publiclands/Pages/western/rockygap.aspx.
Rocky Gap Casino
Try your luck at Rocky Gap Casino on the shores of Lake Habeeb. Not just a place to play the slots, the casino is a full-service resort complete with a golf course and spa. Multiple restaurants offer both indoor and outdoor dining.
Pull up an Adirondack chair next to the lake and sip a cocktail with friends. Or rent a covered paddleboat (with seating for four people) for a leisurely jaunt on the water.
Greenridge State Forest
Greenridge State Forest is the largest contiguous forest in the state at 49,000 acres. The forest avails itself to hikers, mountain bikers, and those on horseback. In addition, the scenic driving tour offers expansive overlooks with views extending into neighboring states.
With 80 miles of trails, the trail system within the park is complex. We chose the Pine Ridge and Twin Oaks trail loop, which combined are approximately 4.2 miles long. We didn’t see another soul as we wandered through dry stream beds and up into the forest.
Cumberland

If the great outdoors isn’t your cup of tea, the city of Cumberland has you covered. The local history and architecture will keep you busy. Although there is much to experience, Cumberland has a small-town vibe and is extremely walkable.
Cumberland was a transportation center in the 19th century. A gateway to the west, this city represented the intersection of the Baltimore & Ohio (B&O) Railroad, the United States’ first National Pike, and the Chesapeake & Ohio (C&O) canal.
The National Road Zero Mile Marker, commemorating the start of the country’s first federal road, can be found near Riverside Park. In its heyday, stagecoaches, canal boats, and trains helped Cumberland to become the second largest city in Maryland. It was also during that time that the city became known as the Queen City.
The city’s rail heritage is celebrated at the Cumberland Railroad Museum. Explore colorful cabooses and learn about rich rail history; the museum is sure to please any train aficionado. Excursions such as the Polar Express Train Rideand Murder Mystery Dinner Trains can be booked via Western Maryland Scenic Railroad (www.wmsr.com).
You can also take a walking tour that will guide you past Victorian buildings and back in time. On the tour you will visit Fort Cumberland, the headquarters for George Washington during periods of the French and Indian War. Check out www.cumberlandwalkingtours.com for more information.
A pedestrian mall along Baltimore Street is at the heart of the arts and entertainment district. Not only will you find stunning buildings, but you’ll also find antique, boutique, and art galleries.
The Allegany Arts Council has year-round educational and arts-related programming as well as revolving exhibits. Step in and revel at the sculpture, paintings, and mixed media from both local and national artists.
C&O Towpath and Canal Place
The C&O Towpath is part of Maryland’s most visited national park, Canal National Historical Park. This 184.5-mile recreational trail traces the C&O Canal and Potomac River from Cumberland to Washington, D.C. Cyclists and hikers regularly enjoy this scenic and historical path.
The shops at Canal Place, located at the head of the towpath, provide a little respite and nourishment. Enjoy wine tasting, farmers markets, and entertainment at the Canal Place festival grounds. I particularly enjoyed chatting with the owner and winemaker at Charis Winery and Distillery.
1812 Brewery
Beer lovers can whet their whistles and sample craft brews at 1812 Brewery. This family-owned business grows its own hops on a 190-acre farm. The tap house is located in a repurposed barn dating back to, you guessed it, 1812.
A large outdoor patio features views of the countryside and a stone fire pit. On the weekends, food trucks and live music supplement the menu.
We enjoyed the atmosphere with one of the most popular brews, the Moro Blood Orange.
Dinner and Dessert
After so much exploring in Allegany County, you’re bound to be ready for a meal. Start with brunch at Allegania Restaurant. This farm-to-table restaurant features Appalachian, Pennsylvania Dutch, and mid-Atlantic cuisine. Outdoor seating with colorful wildflower bouquets is available on the pedestrian mall in downtown Cumberland.
A little closer to Rocky Gap, Pucci serves up delicious items from a broad menu of locally-sourced ingredients. Located in the historic 1818 Hinkle House which served as a Civil War hospital, Pucci specializes in wood-fired pizzas with homemade dough. Grab a seat outside on the heated brick patio and enjoy a slice of spicy buffalo chicken pizza.
For a little dessert, pick a spot along the Allegany Ice Cream Trail which highlights sweet treats from one end of the county to the other. Queen City Creamery churns out fresh frozen custard. Try the flavor of the day or an adult milkshake if you’re feeling adventurous.
The creamery also features a recreated 1940s soda fountain. The ice creamery is within walking distance of Canal Place.
Trail Towns
Allegany County hosts a number of towns along the Great Allegheny Passage. Cumberland and Frostburg are along this 150-mile cycling and hiking trail that connects central Maryland with Pittsburgh. These trail towns are a good basecamp for touring this diverse region. For more information, check out https://gaptrail.org.
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