Ralph Waldo Emerson once warned his frequent hiking companion and fellow nature lover, Henry David Thoreau, that Mt. Greylock was a "serious mountain." Thoreau, of course, climbed it immediately. He summited the 3,491-foot Massachusetts high point via what he described as, in the purplest prose, "a road for the pilgrim to enter upon, who would climb to the gates of heaven." That road is now the 5.5-mile Bellows Pipe Trail.
Hike it by heading 2.2 miles south from North Adams on Notch Road to the trailhead at Notch Gate. The path rises 1,000 feet through the falls-filled ravine between Mt. Greylock and Ragged Mountain. The state's only boreal forest grows here. (Want to make it an overnight? The trail passes a shelter hidden in the pines at mile 2.7.) Link to the Appalachian Trail at mile 3.7 and wind through birch and pines another half-mile to the summit, a flat, open field with a lodge (see right), the Massachusetts Veterans War Memorial (built in 1932), and wide-screen views of the rolling Berkshire Mountains.
Thoreau, of course, didn't have it so cush. He bushwhacked the final part of the ascent and slept on the summit under a plank of wood. And he wasn't rewarded with the now-legendary five-state view. It was socked in, or, in more Thoreauvian terms, obscured by an "undulating valley of clouds." In fall, the panorama draws foliage-heads (the majority drive to the summit on the newly restored road). Return the way you came or make an 11-mile loop with the AT and Bernard Farm Trail. Don't like to share? Wait until snowfall to trek–or snowshoe–in total solitude.
The Civilian Conservation Corps built Bascom Lodge in the 1930s using Greylock's schist and red spruce. You can't beat a bowl of chowder by the fire. Open, weather willing, through November ($35-$100/night).
From the visitor center on Rockwell Rd., take Bradley Farm and Woodson Spring Trails to Round's Rock for a seven-miler with Taconic Range views.
Greylock Gin, made in the Berkshires' first (legal) distillery since Prohibition. berkshiremountaindistillers.com