23. Cumberland, MD
Why go: Take advantage of fall’s perfect cycling weather by riding the Great Allegheny Passage, a 150-mile rail-trail that connects Cumberland, MD, and Pittsburgh, PA. Or you can go the other way: Cumberland’s Mile Marker 0 is where the GAP meets the C&O Canal Towpath National Park, which leads 184 miles east to Washington, D.C.
Where to stay: Bunk down atop Town Hill Mountain at the Town Hill B&B. Not only do you get a bird’s eye view of Allegany County’s foliage (and the mountains of Pennsylvania, Maryland, and West Virginia), the inn also offers a shuttle service to and from the towpath for cyclists.
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