Plan a full day (or two) for your visit to the Western Maryland Rail Trail, a 22-mile paved route that will take you through several eras of American history.
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.
From the trailhead in Hancock, you can head east or west along the trail, about 10 miles in either direction. Whichever direction you choose, expect to pass fields and wooded groves. 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.
The western portion of the Western Maryland Rail Trail is blessed with magnificent views of the Potomac River. Large rock outcroppings will catch your attention, as will the ruins of the Round Top Cement Mill, which was built in the 1830s and was Hancock's largest employer during the Civil War.
To the east, and just past downtown Hancock, you can buy trailside snacks from Blue Goose Fruit Market & Bakery where, in the 1920s, more than 5,000 surrounding acres were planted with fruit trees. Traveling a little farther, you will find historical markers for Little Pool and Park Head cemeteries. Be on the lookout for deer and wild turkey that are not fazed by the loud traffic nearby, nor are the bears that are occassionally spotted in the area.
At trail's end, hop on the C&O Canal towpath and continue just a short distance east to Fort Frederick, well worth a visit. To vary your route, and maximize your scenery, take the Western Maryland Rail Trail in one direction and loop back on the towpath.
Fort Frederick State Park trailhead: From Interstate 70, take Exit 12 to State Route 56 and head east toward Big Pool. The trail parking lot is across the street from the post office.
Hancock trailhead: From I-70, take Exit 3 and travel west on SR 144 for 1.4 miles. There is parking at Hancock Station, just off Main Street.
Sideling Hill Wildlife Management Area trailhead: From I-68, take Exit 77 and head south on Woodmont Road, which will intersect with the trail at Pearre Road. Parking is available.