Top 15 Must-Do Activities in Cumberland, Maryland

Situated within an Appalachian mountain landscape, the city of Cumberland emerged as an industrial hub in the mid-19th century, positioned at a crucial junction in the area’s networks of roads, railroads, and canals.

Today recognized as a prominent tourist destination, Cumberland remains a key crossroads. Visitors can experience the remarkable Western Maryland Scenic Railroad or traverse the 185-mile towpath of the Chesapeake & Ohio Canal.

When combined with the Great Allegheny Passage, this trail offers a continuous hiking or biking route connecting Washington, D.C. and Pittsburgh.

Cumberland also features a British Colonial fort from the 1750s, significant as the site where George Washington first took military command during the French and Indian War (1754-1763).

1. C&O Canal National Historical Park

Cumberland served as the western terminus for an 184.5-mile transportation system, primarily transporting coal from Western Maryland to the Port of Georgetown in Washington, D.C. The project commenced in 1828 and reached Cumberland by 1850, functioning as a vital waterway for cargo until the 1920s.

The canal, alongside its remaining infrastructure and towpath, was designated a National Monument in 1961. Visitors have the opportunity to hike or bike the entire route, encountering diverse attractions ranging from panoramic views of the Potomac Valley to canalside warehouses, historic taverns, aqueducts, and noteworthy engineering achievements such as the Paw Paw Tunnel.

Hiker-biker campsites are available every 5-7 miles along the towpath, complete with water pumps, fire pits, picnic areas, and latrines.

2. Western Maryland Scenic Railroad

In Cumberland, visitors can embark on one of the most scenic railroad journeys in the nation, traversing a section of the historic Western Maryland Railway. The Western Maryland Scenic Railroad transports passengers through the aptly named Cumberland Narrows in the Allegheny Mountains to Frostburg.

The views are spectacular, featuring an elevation gain of 1,300 feet. A standard round-trip journey lasts approximately three and a half hours, including 90 minutes to enjoy the scenic town of Frostburg.

The railroad offers a variety of themed rides throughout the year, including Moonshine Dinner Trains, Murder Mystery Dinner Trains, The Polar Express Train Ride, Ice Cream Trains, Easter Trains, and more. While most locomotives are diesel-powered, the 1949 Baldwin Steam Locomotive Number 1309 is one of the few steam engines in the fleet.

3. Cumberland Visitor Center

Serving as an excellent introduction to adventures along the towpath, the grand 1913 Western Maryland Railway Station features an interactive museum dedicated to the Chesapeake and Ohio Canal. The exhibits cover a wide array of topics related to the canal, with numerous hands-on displays to engage younger visitors.

From an engineering perspective, visitors can explore essential components of the canal system, including models of locks and the remarkable Paw Paw Tunnel. Moreover, the museum provides insight into the canal’s strenuous construction and its connection to various industries, such as boat building and coal, which was the predominant cargo throughout the canal’s operation.

Additionally, the visitor center showcases Cumberland’s importance as a transportation hub in the 19th century and supplies resources for self-guided tours of the historic downtown area.

4. Great Allegheny Passage (GAP)

This extensive 150-mile National Recreation Trail connects Cumberland with Pittsburgh, following the former alignments of several historic railroads. Commencing in the mid-1980s and concluding in 2006 after an $80 million investment, the Great Allegheny Passage showcases some of Maryland and Pennsylvania’s most picturesque landscapes.

Since this is a rail trail, the grade remains gentle, making it accessible for all. Along the route, various detours and significant landmarks are worth exploring, including state parks, viaducts, railroad tunnels, historic bridges, and the Mason-Dixon Line at the Maryland-Pennsylvania border.

5. Washington Street Historic District

Perched atop the hill from the west bank of Wills Creek, the Washington Street Historic District is a National Historic District named in honor of George Washington, who commanded the fort at this location approximately 270 years ago. The earthworks of Fort Cumberland can still be discerned here, particularly on the premises of Emmanuel Episcopal Church.

At one time, this site represented the westernmost outpost of the British Empire and held the distinction of being North America’s largest military installation under Washington’s command. He returned to the site decades later in 1794 to quell the Whiskey Rebellion, and visitors can follow the Fort Cumberland Trail for fascinating information about the installation.

In addition to many of Cumberland’s oldest and most notable homes, the district is also home to the city’s most prominent landmark, the Allegany County Courthouse. Built in the Richardsonian Romanesque style in 1893, this magnificent structure dominates the Cumberland skyline.

6. Canal Place

Cumberland’s vibrant transportation heritage converges at a 58-acre state park marking the western terminus of the C&O Canal. This area comprises the Cumberland Visitor Center, the Western Maryland Railway Station, the Cumberland Basin, and the Allegany Museum.

To signify the city’s status as a historic crossroads, Interstate 68 spans above, while the Great Allegheny Passage intersects with the C&O Canal towpath at this junction. A leisurely stroll around Canal Place reveals numerous smaller details to appreciate, including The Cumberland, a full-size replica of a canal boat that navigated the C&O Canal.

Additionally, there is a large open green space suitable for outdoor events such as the River & Rails Festival in August, along with Cumberland Pride and the Rock the Mountains festival in June.

7. Rocky Gap State Park

Located just a short ten-minute drive from downtown Cumberland, Rocky Gap State Park spans over 3,000 acres of rugged mountainous terrain. At its center lies Lake Habeeb, a 243-acre reservoir established in the 1970s, notable for its strikingly blue waters.

The park features a beach on the lake, with the availability of stand-up paddle boards, kayaks, and canoes available for rent during the summer months, depending on the weather.

Rocky Gap Run feeds into the lake, flowing through a majestic, mile-long gap characterized by sheer cliffs and a rich rhododendron forest that can be enjoyed via an extensive trail system. Another path winds to the summit of Evitts Mountain (2,560 ft), offering scenic views of the lake.

On the water’s edge, the Rocky Gap Casino Resort awaits, featuring a 24-hour casino equipped with over 660 slot machines and 17 table games, along with two bars, a newly added lakeside terrace, a spa, and Maryland’s only Jack Nicklaus signature golf course.

8. Downtown Cumberland Historic District

Baltimore Street, formerly the main thoroughfare of Cumberland, has been repaved with bricks and transformed into a pedestrian mall for three blocks. This environment allows visitors to leisurely appreciate turn-of-the-century commercial architecture and explore a diverse selection of local shops featuring antiques, books, home décor, jewelry, musical instruments, collectibles, and more.

Numerous dining establishments can be found in this area and along intersecting Centre and Liberty Streets. Options include cafes, grills, iconic fast-food establishments, BBQ, pizza, American cuisine, Italian, French, and pan-Asian offerings.

The downtown area also comprises the Cumberland A&E District, which encompasses the Allegany Arts Council (9 N Centre St), along with the Cumberland and Embassy Theatres and the Allegany Museum.

9. Allegany Museum

Located in a beautifully restored 1932 Neoclassical Revival building on Canal Place, the Allegany Museum provides an engaging experience dedicated to the unique heritage of the Allegany area. Originally constructed as a federal building serving as a courthouse and post office, the museum opened its doors in 2010 following an extensive restoration that restored luxurious interior elements, including marble floors, barrel-vaulted ceilings, and intricately carved walnut.

The museum boasts a robust collection of over 50,000 artifacts, offering insights into the region’s prehistory, early Native American inhabitants, European settlement, Fort Cumberland, and local industries such as transportation, glassmaking, brewing, and tire manufacturing.

10. Emmanuel Episcopal Church

Several intriguing aspects define the history of Emmanuel Episcopal Church in the Washington Street Historic District. This church is founded on the very grounds of Fort Cumberland (established in 1754). The fort historically hosted a congregation and evolved into a suitable location for a church following the cessation of its military function.

The current Gothic Revival structure was completed in 1851. Beneath the church, remnants of tunnels and storehouses from the fort persist, serving as a component of the Underground Railroad in the 19th century.

Internally, the church is notable for its exquisite stained glass designed by Louis Comfort Tiffany, which was crafted over two decades in the early 20th century.

11. Allegany Arts Council

The primary organization representing the arts in Allegany County is the Allegany Arts Council, which was established in 1975. The council enhances the community by providing a diverse range of programming across all artistic disciplines. Its headquarters can be found in the Cumberland A&E District, situated on the first floor of a historic commercial structure constructed in the 1890s.

Visitors can explore exhibitions at the Saville Gallery, a spacious environment adorned with original 19th-century features including hardwood floors and a tin ceiling. A new exhibition is presented approximately every month, along with annual hallmark events such as the Mountain Maryland Plein Air Competition & Exhibition, Allegany National Photography Competition & Exhibition, and the Wills Creek Exhibition of Fine Art.

Within the same building, the Schwab Mountain Maryland Gallery provides a more intimate setting and hosts small-scale live performances, workshops, and meetings.

12. Gilchrist Gallery & Museum

This art venue within the Washington Street Historic District is situated in one of Cumberland’s oldest brick residences. The mansion, built in the 1840s, is located within the original stockade of Fort Cumberland and features a Federal-Greek Revival transitional architectural style.

Set amidst beautifully landscaped gardens, the property includes six renovated galleries, a permanent art collection, an art library, and a significant costume collection. From late March until December 24, the Gilchrist Gallery & Museum hosts a series of month-long exhibitions featuring nationally recognized artists across a wide range of mediums.

13. George Washington’s Headquarters

Washington’s quarters and office at Fort Cumberland have been preserved and relocated from the hilltop to the bank of Wills Creek, just across the water from Canal Place. Completed around 1754-1755, Washington utilized this log cabin intermittently until 1758, and again upon his return to suppress the Whiskey Rebellion in 1794.

This structure is the last remaining building from the fort. Although entry is not permitted, visitors can peer through the windows to catch a glimpse of the interior, reflecting Washington’s time.

14. Paw Paw Tunnel

The Paw Paw Tunnel is regarded as the most significant engineering achievement along the C&O Canal, extending 3,118 feet and located approximately 25 miles east of Cumberland. This tunnel circumvents the Paw Paw Bends, a series of five horseshoe curves spanning six miles along the Potomac River.

Without this substantial infrastructure, Cumberland’s economic success in the 19th century would have been unattainable. The construction, which took 14 arduous years (1836-1850) and amassed costs exceeding six million dollars, nearly bankrupted the Chesapeake and Ohio Canal Company.

The towpath runs through the tunnel, and a flashlight is advised for navigation, as visitors may encounter a few bats along the way. Additionally, you can traverse the looping Tunnel Hill Trail, which spans two miles and features interpretive signs detailing the Irish and German workers who resided by the path during the tunnel’s lengthy construction process.

15. Sideling Hill Overlook

The construction of Interstate 68 is a critical aspect of modern Cumberland’s narrative, traversing throughout the city and the surrounding mountainous terrain. One of the more striking sights along this highway is the extraordinary road cut at Sideling Hill, situated approximately 30 miles east of Cumberland.

This dramatic escarpment reveals a 340-foot deep cleavage in the landscape, providing an insightful view into the mountain ridge’s geological characteristics, particularly the downward-folded strata positioned between two upfolded anticlines, all capped with erosion-resistant conglomerate.

A rest area, pedestrian bridge, and stairway facilitate contemplation of the views while providing historical information about the 19th-century National Road, which ran parallel to I-68 from Keysers Ridge to Hancock.