Resting in an Appalachian mountainscape, the city of Cumberland developed as an industrial center in the mid-19th century at a nexus point in the region’s road, railroad and canal networks.
Now a destination for tourists, Cumberland is still a crossroads, and you can ride the awe-inspiring Western Maryland Scenic Railroad, or travel the 185-mile towpath of the Chesapeake & Ohio Canal.
Cumberland is also the site of a British Colonial fort from the 1750s, important today for being the place where George Washington first assumed military command, during the French and Indian War (1754-1763).
1. C&O Canal National Historical Park
Cumberland was the western terminus for an 184.5-mile transportation system, mostly hauling coal from Western Maryland to the Port of Georgetown in Washington, D.C.
The project was started in 1828, and finally reached Cumberland in 1850, serving as an important waterway for cargo until the 1920s.
The canal, its surviving infrastructure and towpath were designated a National Monument in 1961.
You can hike or bicycle the entirety of the route, and there’s tons to see, from the stirring scenery of the Potomac Valley to canalside warehouses, old taverns, aqueducts, historic mile markers, locks and dumbfounding pieces of engineering like the Paw Paw Tunnel.
There are hiker-biker campsites every 5-7 miles along the towpath, each one with a water pump, firepit, picnic area and latrine.
2. Western Maryland Scenic Railroad
In Cumberland you can embark on one of the most spectacular railroad journeys in the country along a stretch of the old Western Maryland Railway.
The Western Maryland Scenic Railroad takes you through the aptly named Cumberland Narrows in the Allegheny Mountains to the town of Frostburg.
The vistas are unforgettable, and there’s a 1,300-foot gain in elevation along the way. A typical round-trip takes 3 ½ hours, and includes 90 minutes to enjoy scenic Frostburg.
The railroad offers themed rides throughout the year, with Moonshine Dinner Trains, Murder Mystery Dinner Trains, The Polar Express Train Ride, Ice Cream Trains, Easter Trains and much more.
Most of the locomotives are diesel powered, but the 1949 Baldwin Steam Locomotive Number 1309 is one of a couple of steam engines in the fleet.
3. Cumberland Visitor Center
The perfect primer for an adventure along the towpath, the grand 1913 Western Maryland Railway Station has an interactive museum about the Chesapeake and Ohio Canal.
The museum covers all aspects of the canal, and the many hands-on exhibits will keep children engaged. From an engineering standpoint you can check out key components in the canal system, with models of locks and the extraordinary Paw Paw Tunnel.
There’s also information about the canal’s arduous construction, and the many industries associated with the canal, such as boat building and coal, which was the main cargo throughout the waterway’s lifespan.
Finally, the visitor center explores Cumberland’s status as a transportation crossroads in the 19th century, and provides maps for self-guided tours of the historic downtown.
4. Great Allegheny Passage (GAP)
A mammoth project, this 150-mile National Recreation Trail connects Cumberland with Pittsburgh, along the former right-of-way of a series of historic railroads.
The Great Allegheny Passage was begun in the mid-1980s and after an investment of $80 million was finally completed in 2006.
You’ll understand the effort as you traverse some of Maryland and Pennsylvania’s most scenic landscapes, and yet because this is a rail trail the grade is always light.
There’s a catalog of detours and important landmarks on the route, like mountainous state parks, viaducts, railroad tunnels, historic bridges and, of course, the Mason-Dixon Line at the border of Maryland and Pennsylvania.
5. Washington Street Historic District
On the hill that climbs sharply from the west bank of Wills Creek is a National Historic District named for George Washington, who commanded the fort here some 270 years ago.
It’s easy to make out the earthworks of Fort Cumberland, especially on the grounds of Emmanuel Episcopal Church.
The fort was the westernmost outpost of the British Empire, this was the largest military installation in North America for a short time, under the leadership of George Washington.
He returned to this place decades later in 1794 to suppress the Whiskey Rebellion. You can follow the Fort Cumberland Trail here, for captivating info about the installation.
As well as many of Cumberland’s oldest and grandest homes, the Washington Street Historic District is home to the city’s most prominent landmark.
This is the Allegany County Courthouse, built in the Richardsonian Romanesque style in 1893 and dominating the Cumberland skyline.
6. Canal Place
Cumberland’s riveting transport heritage coalesces around a 58-acre state park marking the western terminus of the C&O Canal.
This incorporates the Cumberland Visitor Center, the Western Maryland Railway Station, the Cumberland Basin and the Allegany Museum.
To remind you that you’re at a great crossroads, the I-68 even passes overhead, while the Great Allegheny Passage meets the C&O Canal towpath at this spot.
There are several smaller details to admire on a walk around Canal Place. One, along Trestle Walk is The Cumberland, a full-size replica of the kind of canal boat that navigated the C&O Canal.
There’s also a large, open green space for outdoor events, like the River & Rails Festival in August, and Cumberland Pride and the Rock the Mountains festival in June.
7. Rocky Gap State Park
Just ten minutes from downtown Cumberland, Rocky Gap State Park preserves more than 3,000 acres of rugged mountain scenery.
At the center is Lake Habeeb, a 243-acre reservoir dammed in the 1970s and renowned for the mesmerizing blueness of its waters.
There’s a beach on the lake, and you can rent stand-up paddle boards, kayaks and canoes in the summer months, weather permitting.
Feeding the lake is Rocky Gap Run, which courses through a majestic, mile-long gap with sheer cliffs and rhododendron-rich hemlock forest that can be savored on a trail. Another trail winds its way to the top of Evitts Mountain (2,560 ft), overlooking the lake.
Finally, on the water’s edge is the Rocky Gap Casino Resort, with a 24-hour casino that has 660+ slot machines and 17 table games, complemented by two bars, a new lakeside terrace, a spa and Maryland’s only Jack Nicklaus signature golf course.
8. Downtown Cumberland Historic District
Baltimore Street, which was once Cumberland’s main thoroughfare for traffic, has been paved with bricks and turned into a pedestrian mall for three blocks.
So you can take your time to soak up the turn-of-the-century commercial architecture and browse a whole directory of local stores, for antiques, books, home design, jewelry, musical instruments, collectibles, video games and much more.
There’s no lack of dining options here and on intersecting Centre and Liberty St, with cafes, grills, long-standing fast food joints, BBQ, pizza, pub fare, contemporary American, Italian, French and pan-Asian.
Downtown also contains the Cumberland A&E District, with the Allegany Arts Council (9 N Centre St), along with the Cumberland and Embassy Theatres and the Allegany Museum.
9. Allegany Museum
In a restored 1932 Neoclassical Revival building on Canal Place there’s a first-class museum dedicated to the unique heritage of the Allegany area.
This was originally a federally constructed building, serving as a courthouse and post office. The Allegany Museum opened here in 2010 following a thorough restoration recovering opulent interior details like marble floors, barrel-vaulted ceilings and carved walnut.
The museum has a rich collection of more than 50,000 items, for insights into the area’s prehistory, early Native American residents, European settlement, Fort Cumberland and industries like transportation, glassware, brewing and tire manufacturing.
10. Emmanuel Episcopal Church
There are many exciting facets to the story of this church in the Washington Street Historic District.
For one, Emmanuel Episcopal Church is built on the very earthworks of Fort Cumberland (1754). The fort had always had a congregation, and became the logical place for a church after losing its military purpose.
The current Gothic Revival building was completed in 1851. Tunnels and storehouses from the fort survive beneath the church and were part of the Underground Railroad in the 19th century.
The church is also significant for interior fittings and magnificent stained glass designed by Louis Comfort Tiffany over the course of two decades in the early 20th century.
11. Allegany Arts Council
The official umbrella organization for the arts in Allegany County is the Allegany Arts Council, founded in 1975, enriching the community with a diversity of programming for all disciplines.
Appropriately, the headquarters can be found in the Cumberland A&E District, on the first floor of an historic commercial building constructed in the 1890s.
You can take in an exhibition at the Saville Gallery here, which is a marvelous, lofty space, with original 19th-century features including hardwood floors and tin ceiling.
There’s a new show roughly every month at this gallery, and a few annual landmark events are the Mountain Maryland Plein Air Competition & Exhibition, Allegany National Photography Competition & Exhibition, and the Wills Creek Exhibition of Fine Art.
In the same building, the Schwab Mountain Maryland Gallery is more intimate and also stages small-scale live performances, workshops and meetings.
12. Gilchrist Gallery & Museum
This art attraction in the Washington Street Historic District is housed by one of Cumberland’s oldest brick residences.
The mansion was built in the 1840s, within the original stockade of Fort Cumberland, in a Federal-Greek Revival transitional style.
The house is wreathed in gorgeous landscaped gardens and contains six renovated galleries, a permanent art collection, an art library and an important costume collection.
Late March through December 24, the Gilchrist Gallery & Museum hosts a series of month-long exhibitions for nationally recognized artists in a wide range of mediums.
13. George Washington’s Headquarters
Washington’s living quarters and office at Fort Cumberland has been preserved and relocated from hilltop down to the edge of Wills Creek, across the water from Canal Place.
Completed around 1754-1755, Washington used this log cabin on and off until 1758, and again when he returned to quell the Whiskey Rebellion in 1794.
This is the only remaining structure from the fort. The cabin can’t be entered but you can look through the windows for a sense of what the interior might have been like in Washington’s time.
14. Paw Paw Tunnel
The single greatest engineering feat along the C&O Canal is this 3,118-foot tunnel, around 25 miles east of Cumberland.
The Paw Paw Tunnel bypasses the Paw Paw Bends, a sequence of five horseshoe bends on Potomac River, six miles in length.
Cumberland’s economic growth in the 19th century would not have been possible without this incredible piece of infrastructure, requiring 14 painstaking years of construction (1836-1850), more than six million and almost bankrupting the Chesapeake and Ohio Canal Company in the process.
The towpath passes through the tunnel, and you’ll need a flashlight as you go, and you should see a few bats.
You can also walk the looping Tunnel Hill Trail, which is two miles long and has interpretive signs detailing the Irish and German workers who lived by the path during the tunnel’s long construction.
15. Sideling Hill Overlook
For better or worse the I-68 is an integral part of modern Cumberland’s story, running right through the city and coursing through the surrounding mountainscape.
One of the most arresting sights along the highway is about 30 miles east of Cumberland, where an epic road cut was made at Sideling Hill.
A massive cleft in the landscape, the road cut is 340 feet deep and gives you a satisfying view of the mountain ridge’s geology, in particular the downward-folded strata between two upfolded anticlines, all topped with erosion-resistant conglomerate.
There’s a rest area, pedestrian bridge and stairway so you can soak up the views and learn about the 19th-century National Road, paralleling I-68 between Keysers Ridge and Hancock.