A National Historic Park at the center of Cumberland in the very attractive Downtown Historic District (along Baltimore St), including the historic Western Maryland Railway Station, a canal boat, festival grounds, an ice-skating rink, and Washington's Headquarters
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The first winery and distillery in Cumberland. They do tastings and sell bottles of their wine and spirits.
An impressive Gothic church in the historic downtown, which was built upon the former site of Fort Cumberland, where George Washington began his military career.
A 20-mile (32-km) section of the Great Allegheny Passage, a trail leading from Pittsburgh to Washington, D.C. and paralleling the Western Maryland Scenic Road. The hike to Frostburg is about 10.5 miles (17 km). The hike to Pittsburgh or D.C. is considerably longer!
A restored Art Deco movie palace from the old days of the Queen City, now functioning as a downtown performance theater in a lovely setting.
The city's most prominent building, which looms over the Cumberland skyline, is very pretty.