20 Best Things to Do in Cumberland, Maryland

By VI Staff on June 1, 2022 - Updated

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Cumberland is a friendly, cultural city with a thriving arts community and a rich history. Hailed as the ‘Gateway to the West,’ for the pioneers of America, Cumberland was once a military outpost operated by George Washington and has several excellent museums that document the history of the city and the region. There are also plenty of outdoor activities to enjoy from hiking and mountain biking to horseback riding, picnicking, and visiting the nearby state parks. Certain attractions may be temporarily closed or require advance reservations. Hours/availability may have changed.

1.Great Allegheny Passage, Cumberland, MD

The Great Allegheny Passage is a rail-trail system featuring a network of long-distance hiker-biker trails that extends through the Allegheny region of the Appalachian Mountains, boasting breath-taking natural scenery. Connecting Washington, D.C. to Pittsburgh in Pennsylvania, the 335-mile trail offers a long-haul adventure for hikers and bikers alike, as well as shorter trips between towns along the way. Once the railway for freight trains between the two cities, the now converted multi-use trail gently winds its way along the Youghiogheny River through the Laurel Highlands and connects with the C&O Canal towpath.

Cumberland, Maryland

2.Rocky Gap State Park, Cumberland, Maryland

The Rocky Gap State Park is a public recreation area seven miles east of Cumberland in Allegany County that offers a variety of attractions, outdoor activities, and camping facilities. The 3,000-acre park is home to spectacular natural landscapes of dramatic cliffs and deep gorges harrowing overlooks and dense verdant hemlock forests. Attractions in the park include the towering Evitts Mountain, the 243-acre Lake Habeeb, and the privately owned and operated Rocky Gap Casino Resort. A large campground has 278 campsites and recreational activities in the park include hiking, mountain biking, boating, fishing and swimming in the lake, and climbing.

12900 Lake Shore Dr, Flintstone, MD 21530, Phone: 301-722-1480

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3.C&O Canal - Paw Paw Tunnel, Cumberland, MD

Forming part of the Chesapeake and Ohio Canal in Allegany County, the Paw Paw Tunnel is a 3,118-foot-long canal tunnel that was built to bypass a six-mile stretch of the Potomac River with five tightly curved horseshoe-shaped bends known as the Paw Paw Bends. Named after a local fruit, the Paw Paw Tunnel had a tumultuous history with construction beginning in 1836 and seeing a lot of fighting and rioting among the workers during its construction. On completion, the 24-foot tall tunnel was 3,000-foot-long and used by canal boats pulled by mules. Eventually, the tunnel was abandoned and, as legend has it, is haunted to this day.

Chesapeake and Ohio Canal Towpath, Oldtown, MD 21555, Phone: 301-722-8226

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4.Western Maryland Scenic Railroad, Cumberland, MD

Offering an exciting mix of rich transportation history and spectacular mountaintop scenery, the Western Maryland Scenic Railroad is a heritage railroad that operates from Cumberland to Frostburg. Using both diesel-powered and steam locomotives, the train begins its journey in downtown Cumberland and travels on ex-Western Maryland Railway trackage through the Allegheny Mountains to downtown Frostburg. Notable attractions along the way include an iron truss bridge, the harrowing Helmstetter’s Horseshoe Curve, and the 914-foot Brush Tunnel that runs beneath Piney Mountain. The tracks join the old Cumberland & Pennsylvania Railroad before reaching Frostburg.

13 Canal St, Cumberland, MD 21502, Phone: 301-759-4400

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5.C&O Canal National Historical Park and Allegany County Visitor Center, Cumberland, MD

The Chesapeake and Ohio Canal National Historical Park was established in 1961 to preserve the neglected remains of the Chesapeake and Ohio Canal. Founded as a National Monument by President Dwight D. Eisenhower, the historical park features a museum that documents the history of the area through interactive and educational displays. Notable attractions at the museum include a model of the Paw Paw Tunnel, exhibits showcasing the day-to-day life of the canal families, a model lock and old boat building, and the lovable Mutt the mule who was famous for pulling canal boats.

13 Canal Street Cumberland, MD 21502, Phone: 301-777-5132

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6.Allegany Museum, Cumberland, Maryland

Located on Pershing Street in Historic Downtown Cumberland, the Allegany Museum is a world-class museum that documents the rich history of Allegany County and the cultural, commercial, and geographic heritage of Appalachian Maryland throughout the eras. Designed by local architect, R. Holt Hitchins in the Art Deco and Neoclassical styles, the building was constructed as a US Court House and Post Office in 1932 and features beautiful finishes in marble and walnut, intricate detailing, and a 3,4000 square foot Grand Courtroom. Today, the building houses the museum houses a collection of over 50,000 items that trace the history of the region from the first Native American residents to the age of industrialization in the 19th and 20th centuries.

3 Pershing St, Cumberland, MD 21502, Phone: 301-777-7200

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7.Emmanuel Episcopal Church, Cumberland, Maryland

Located on Washington Street at the eastern end of the Washington Street Historic District, the Emmanuel Episcopal Church of Cumberland is a striking example of early Gothic Revival architecture. Built on the foundations of Fort Cumberland, the famous military outpost where George Washington began his career, the Emmanuel Episcopal Church of Cumberland is the historic home of the Emmanuel parish that was founded in 1803. Designed by Philadelphia architect John Notman, the church was built in 1849 and still features beautiful original elements like Tiffany stained-glass windows spanning three different periods and a scale model of Fort Cumberland. The magnificent church, parish house, and grounds are part of the Fort Cumberland Walking Trail.

16 Washington St, Cumberland, MD 21502, Phone: 301-777-3364

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8.George Washington's Headquarters, Cumberland, Maryland

Set on Greene Street in the historic downtown district of Cumberland, the Headquarters of George Washington is a renowned historic site that is famous for being the place where George Washington slept during the French and Indian War. Originally based at Fort Cumberland and relocated after the Fort’s destruction, the one-room cabin is closed to the public and houses a unique collection of historical displays and period artifacts, flags, weaponry, and a life-size wax reproduction of Washington himself, which visitors can view through the windows.

38 Greene St, Cumberland, MD 21502, Phone: 301-759-6636

9.Cumberland Narrows, Cumberland, MD

The Cumberland Narrows, also known simply as ‘The Narrows’ is a 1,000-foot-deep scenic gorge cut by Wills Creek through the Allegheny Mountains that create a natural east-west gateway between Wills and the Haystack mountains. Originally an Indian footpath, the gorge was discovered by British troops in 1755 as they tried to cross the mountains to attack the French in the Ohio River Valley. It was later developed into a major federally funded highway known as the National Pike, however, the gorge is now bypassed by Interstate 68.

Cumberland, MD 21502

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10.Allegany Fairgrounds, Cumberland, Maryland

The Allegany County Fairgrounds is a vast expanse of land that hosts the annual Allegany County Fair & Ag Expo. Founded over 30 years ago to host the fair, the 120-acre fairgrounds have several features, including an 18,000square-foot pavilion, a half-mile dirt race track bordered by a 3,000-seat grandstand, and a vast 25,000 square foot multi-purpose building for indoor exhibits. Held over a week every July, the fair hosts a variety of exhibits, musical performances and live acts, firework shows, demolition derbies, and an array of rides and attractions for the whole family.

11490 Moss Avenue Ext., Cumberland, Maryland 21502

11.The Gordon-Roberts House, Cumberland, MD

The Gordon-Roberts House is a beautifully preserved Victorian home built for the President of the C&O Canal, Josiah Gordon in 1867. After 20 years of residence, the Gordons sold the house to W. Milnor Roberts and his family, and the house is named for the two families that lived in it. Today, the house operates as a museum that offers a sample of life in the late 1800s and features rooms filled with period furnishings, clothing, toys, and music. Operated by the Allegany County Historical Society, the museum is open Wednesday through Saturday and costumed docents offer guided tours on the hour.

218 Washington St, Cumberland, MD 21502, Phone: 301-777-8678

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12.Cumberland Theatre, Cumberland, Maryland

The Cumberland Theatre is a regional professional theater that presents a wide range of performances ranging from plays and comedies to dramas and musicals. Founded in 1988, the theater is based in a former church on North Johnson Street after being relocated in 1991 and houses a 198-seat theater with state-of-the-art acoustics and sound, costume and scene shops, and storage spaces. During each production, the lobby of the theater serves as a space for the Bev Walker Gallery and displays local and regional artworks.

101 Johnson St, Cumberland, MD 21502, Phone: 301-759-4990

13.Allegany County Courthouse, Cumberland, Maryland

Located in the heart of Cumberland's Washington Street Historic District, the Allegany County Courthouse is the primary Circuit Court for Allegany County in Maryland. Built in 1799, the building is an architectural gem that dominates the skyline of the city, purposely constructed to instill respect and recognition.

30 Washington St, Cumberland, MD 21502, Phone: 301-777-5923

14.C. William Gilchrist Museum of the Arts, Cumberland, MD

The C. William Gilchrist Museum of the Arts is a beautifully preserved early 19th-century Federal mansion dedicated to the culture and history of Allegany County and the state of Maryland. Surrounded by pristinely manicured gardens on Washington Street, the museum features six spacious galleries that house a rotating schedule of art exhibits and theme-oriented presentations across various media forms. The museum also houses an impressive art library and offers art classes and lectures for budding artists and doyennes.

104 Washington Street, Cumberland, Maryland 21502

15.Things to Do Near Me: F. Brooke Whiting House and Museum, Cumberland, MD

The F. Brooke Whiting House & Museum is a historic bungalow dating back to 1911 that houses a collection of artworks and decorative arts from Asia, America, and Europe. Once the residence of Brooke Whiting, a prominent attorney and worldwide connoisseur from Cumberland, the bungalow features a world-class art collection gathered by Whiting on his extensive travels around the world. The museum hosts a variety of lectures, workshops, and symposiums, as well as a Fourth Friday series that local artists, actors, writers, art specialists.

218 Washington St, Cumberland, MD 21502, Phone: 301-777-7782

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16.Things to Do in Cumberland, Maryland: Allegany Arts Council

The Allegany Arts Council was founded in 1975 to oversee the arts world in Allegany County. Located on Centre Street in the heart of Downtown Cumberland's Arts & Entertainment District, the Allegany Arts Council manages all the artistic disciplines in the region, ranging from theatrical performances, live entertainment, art exhibitions, and literary readings. The Downtown Cumberland facility also houses the Saville Gallery and a small Community Room that is used for an array of functions and events like classes, workshops, and lectures.

9 N Centre St, Cumberland, MD 21502, Phone: 301-777-2787

17.Things to Do Near Me: Embassy Theatre, Cumberland, Maryland

The Embassy Theatre is a community art and performance center on Baltimore Street in downtown Cumberland that presents a repertoire of classic films, local and national theater, live music, and dance performances. Housed in a beautifully preserved Art Deco movie house dating back to 1931, the multi-purpose center aims to promote the arts with a full calendar of events and shows, including local dramas and comedies. Current schedules and tickets can be obtained from the Embassy lobby's Passport Café.

49 Baltimore St, Cumberland, MD 21502, Phone: 240-362-7183

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18.Things to Do in Cumberland, Maryland: Ristorante Ottaviani

Ristorante Ottaviani is an Old-World, family-run eatery that serves traditional Italian fare, classic steaks, and fresh seafood in a warm and convivial setting. Boasting comfortable décor with wooden floors, Tuscan hues, and two dining levels, the restaurant serves a menu of authentic Italian and Mediterranean cuisine, featuring fresh seafood, prime steaks, handmade pasta, wood-fired pizzas, and decadent desserts made from age-old family recipes. A full-service bar offers a wide range of libations from casual Italian wines and craft beers to global wines, draft and tap brews and signature cocktails made with imported spirits. Ristorante Ottaviani is open for dinner only, nightly.

25 N Centre St, Cumberland, MD 21502, Phone: 301-722-0052

19.Puccini Restaurant, Cumberland, Maryland

Housed in the historic 1818 Hinkle House on Ali Ghan Road that once served as a Civil War hospital during the Battle at Folck’s Mill, Puccini Restaurant is an elegant Italian eatery with a warm and welcoming ambiance that serves authentic Italian and Mediterranean cuisine. Featuring exposed brick walls and cozy, candlelit dining nooks that are ideal for romantic trysts, the family-owned restaurant specializes in hand-tossed, thin-crust, and wood-fired pizza with a variety of delicious toppings and house-made sauces. The cuisine is accompanied by a curated wine list featuring wines from Italy and other wine-growing countries around the world, craft beers on tap and by the bottle, handcrafted cocktails, and high-end spirits. Puccini Restaurant is open for lunch and dinner, daily.

12901 Ali Ghan Rd NE, Cumberland, MD 21502, Phone: 301-777-7822

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