Cumberland, Maryland - Things to See and Do

Things to see and do at Cumberland, Maryland

Visited September 2025

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Cumberland, Maryland: A Historic Gateway to the Mountains

Tucked into the scenic foothills of the Appalachian Mountains, Cumberland, Maryland is a city where history, culture, and outdoor adventure come together. Known as the “Queen City,” Cumberland was once a key transportation hub during America’s westward expansion. Today, it’s a lively small city with historic charm, vibrant arts, and access to some of the region’s best hiking and biking trails.

Why Visit Cumberland, MD?

Cumberland is the gateway to western Maryland’s natural beauty and rich history. With its historic downtown, thriving arts district, and proximity to trails like the Great Allegheny Passage and the C&O Canal Towpath, Cumberland offers plenty for visitors seeking both relaxation and adventure. Just two hours from Washington, D.C. and Baltimore, it makes for an easy weekend getaway.

Top Things to Do in Cumberland, Maryland

1. Explore Historic Downtown Cumberland

Downtown Cumberland is filled with historic architecture, boutique shops, and art galleries. The Baltimore Street pedestrian mall is a hub for dining, live music, and seasonal festivals.

2. Ride the Western Maryland Scenic Railroad

Step back in time with a ride on the Western Maryland Scenic Railroad, which runs from Cumberland to Frostburg. The journey winds through mountain scenery and includes restored vintage locomotives, making it one of the city’s most popular attractions.

3. Walk or Bike the C&O Canal Towpath

Cumberland is the western terminus of the Chesapeake & Ohio Canal National Historical Park. The towpath trail stretches 184.5 miles to Washington, D.C., offering opportunities for biking, hiking, and exploring historic canal structures.

4. Connect with the Great Allegheny Passage

Outdoor enthusiasts love Cumberland as the starting point for the Great Allegheny Passage (GAP), a 150-mile trail that connects to Pittsburgh. Together with the C&O Canal Towpath, it forms a continuous 335-mile trail from Pittsburgh to D.C.

5. Visit Local Museums and Historic Sites

Allegany Museum: Showcasing local history and culture.
Gordon-Roberts House: A beautifully preserved Victorian-era home.
George Washington’s Headquarters: A log cabin once used by the first president during the French and Indian War.

Where to Eat and Stay

Cumberland offers a variety of dining options, from cozy cafés to craft breweries. Local favorites include hearty Appalachian fare and Maryland specialties. For lodging, choose from historic inns, modern hotels, or bed-and-breakfasts. The Fairfield Inn in a historic building downtown combines comfort with charm.

Best Time to Visit Cumberland, MD

Cumberland is a year-round destination. Spring and summer are perfect for cycling and festivals, fall brings vibrant foliage across the mountains, and winter offers a quieter atmosphere with nearby skiing at Wisp Resort just an hour away.

Plan Your Trip to Cumberland

With its historic sites, trails, and mountain scenery, Cumberland, Maryland is a destination that perfectly blends history and outdoor adventure. Whether you’re biking the C&O Canal, riding the scenic railroad, or enjoying a stroll through downtown, Cumberland offers something for everyone.

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