Looking for a scenic mountain getaway packed with history and outdoor adventures? Head to Cumberland! Nestled in the foothills of the Allegheny Mountains, Cumberland offers charming historic streets, bike trails, riverfront parks, and beautiful mountain views. Whether you’re into history, hiking, or artsy downtown strolls, Cumberland delivers small-town warmth with big outdoor experiences.

Best Time to Visit

The best time to visit Cumberland is during spring and fall (April–June and September–October). Comfortable temperatures and colorful mountain scenery make it perfect for hiking, biking, and enjoying local festivals.

How to Get There

  • If you are traveling by car: Cumberland is located along Interstate 68, about 2 hours from Pittsburgh, PA, and 2.5 hours from Washington, D.C.
  • By Train: Amtrak’s Capitol Limited line connects Cumberland with Washington, D.C., and Chicago, offering beautiful mountain views along the way.
  • By Plane: The nearest major airports are Pittsburgh International Airport (PIT) and Washington Dulles International Airport (IAD), each about 2–2.5 hours away.

Where to Stay

  • Fairfield Inn & Suites Cumberland – Comfortable hotel steps from the C&O Canal towpath and the downtown arts district.
  • Rocky Gap Casino Resort – Lakeside resort featuring a casino, golf course, spa, and access to Rocky Gap State Park trails.
  • Bruce House Inn – Elegant historic bed-and-breakfast located near downtown with charming period décor and a relaxing atmosphere.

Best Things to Do

Bike or Hike Scenic Wonders on the Great Allegheny Passage

Bike or Hike Scenic Wonders on the Great Allegheny Passage

© Leart/stock.adobe.com

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. Facebook

Escape to Nature’s Playground at Rocky Gap State Park

Escape to Nature’s Playground at Rocky Gap State Park

© Oleksii Sergieiev/stock.adobe.com

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

Activities and Attractions for Couples:

Journey Through History in the C&O Canal’s Paw Paw Tunnel

Journey Through History in the C&O Canal’s Paw Paw Tunnel

© Lydia/stock.adobe.com

Forming part of the Chesapeake and Ohio Canal in Allegany County, the C&O Canal - 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

Ride Through Time on the Western Maryland Scenic Railroad

Ride Through Time on the Western Maryland Scenic Railroad

© evannovostro/stock.adobe.com

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.

Western Maryland Scenic Railroad, 13 Canal St, Cumberland, MD 21502, Phone: 301-759-4400

If You Love History and Heritage, Stop by the C&O Canal National Historical Park

If You Love History and Heritage, Stop by the C&O Canal National Historical Park

© Zack Frank/stock.adobe.com

The C&O 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

Explore Local Stories at the Allegany Museum

Explore Local Stories at the Allegany Museum

© Allegany Museum

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

What to do if you are traveling with kids:

Step Into the Past at George Washington’s Headquarters

Step Into the Past at George Washington’s Headquarters

© Sucha Kittiwararat/stock.adobe.com

Set on Greene Street in the historic downtown district of Cumberland, George Washington's Headquarters 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

Marvel at Natural Beauty in the Cumberland Narrows

Marvel at Natural Beauty in the Cumberland Narrows

© den-belitsky/stock.adobe.com

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

If You’re Ready for Classic Fun, Head to the Allegany Fairgrounds

If You’re Ready for Classic Fun, Head to the Allegany Fairgrounds

© Allegany Fairgrounds

The Allegany 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

Must-see if you are a first-time visitor:

  • Bike or walk the C&O Canal Towpath – Enjoy 184.5 miles of scenic trails along the Potomac River starting in downtown Cumberland.
  • Explore the Cumberland Historic District – Wander charming streets lined with boutiques, art galleries, cafés, and historic architecture.

Where to Eat

  • Ristorante Ottaviani – Cozy Italian restaurant downtown known for homemade pasta and a romantic setting.
  • Queen City Creamery – Classic diner and creamery offering delicious breakfast, sandwiches, and homemade frozen custard.
  • Corner Tavern & Café – Casual spot for craft beers, hearty American fare, and live local music in a welcoming atmosphere.

If you are interested in local events:

  • Heritage Days Festival (June) – Celebrate Cumberland’s rich history with reenactments, artisan booths, food, and live entertainment downtown.
  • Mountain Maryland Plein Air Festival (May) – Watch artists capture the region’s stunning landscapes in real time during this popular arts festival.
  • Downtown Cumberland Christmas Market (December) – Holiday festivities with market vendors, carolers, light displays, and horse-drawn carriage rides.

If you are looking for unique day trips within 30 Minutes of Cumberland, Maryland:

  • Frostburg, MD (20 min) – Visit a lively college town with craft breweries, art galleries, and the Frostburg State University campus.
  • Green Ridge State Forest (30 min) – Explore over 47,000 acres of rugged wilderness, scenic drives, and hiking trails.
  • Paw Paw Tunnel (30 min) – Hike through this historic 3,118-foot canal tunnel along the C&O Canal Towpath in West Virginia.
  • Dans Mountain State Park (25 min) – Enjoy a scenic drive, hiking trails, a public swimming pool, and beautiful mountain overlooks.
  • Great Allegheny Passage Trail (0 min) – Start your bike journey on this famed rail trail heading northwest from Cumberland toward Pittsburgh.

Frequently Asked Questions:

  • Where is Cumberland, Maryland located?
    • Cumberland is a friendly, cultural city in Maryland, known for its thriving arts community and rich history.
  • What is the historical significance of Cumberland?
    • Cumberland was once a military outpost operated by George Washington, playing a key role in early American history.
  • Are there museums in Cumberland?
    • Yes! Cumberland has several excellent museums that document the history of the city and the surrounding region.
  • What outdoor activities are available in Cumberland?
    • Visitors can enjoy a variety of outdoor activities, including:
      • Hiking
      • Mountain biking
      • Horseback riding
      • Picnicking
      • Exploring nearby state parks

At a Glance:


Best Time to Visit Places to Stay Tips for Visiting
Spring (March-May) – Mild temperatures and blooming mountain scenery. Fairfield Inn & Suites Cumberland – A comfortable stay near the downtown area. Bike the Great Allegheny Passage – Enjoy scenic trails along the Potomac River.
Summer (June-August) – Warm weather, perfect for outdoor exploration. Rocky Gap Casino Resort – A lakeside resort with a golf course and gaming options. Explore Rocky Gap State Park – Hike, boat, or relax on the sandy beach by Lake Habeeb.
Fall (September-November) – Crisp air and breathtaking fall foliage. The Bruce House Inn – A charming historic bed & breakfast. Ride the Western Maryland Scenic Railroad – Take a vintage train ride through colorful autumn landscapes.
Winter (December-February) – Cold and snowy, ideal for a cozy retreat. Hampton Inn Cumberland – A cozy and convenient lodging option. Visit Downtown Cumberland’s Winter Markets – Enjoy holiday lights, shopping, and seasonal treats.

Map:


Plan Your Trip