Western Maryland Rail Trail

You can access this trail from many points, but the main trailhead is in the quaint town of Hancock (population 1,750). Stop here for food, drinks, antique shopping, to stay the night or just to wander around the historical downtown, which was once Maryland's frontier and frequently visited by George Washington, among other notables.

The rail-trail parallels the Chesapeake and Ohio Canal, a 185-mile, unpaved towpath that was used to transport coal from Cumberland, Maryland, to the port of Georgetown in Washington, D.C., from 1828 until 1924. The route's historical sites include the canal's locks and lock houses. Along the 22 miles of the WMRT, you'll find nine connections between it and the C&O Canal Towpath.

Length: 22 miles
Trail end points: Big Pool Rd. near Fort Frederick State Park to Old Pearre Rail Station (Sideling Hill WMA)

Info: http://www.traillink.com/trail/western-maryland-rail-trail.aspx