The trail utilizes two distinct ridgelines of the Taconic Mountains. From Route 20 north, the trail passes through Pittsfield State Forest in Massachusetts; features include the highland Cranberry Pond and Twin Ponds, Doll Mountain, Smith Mountain, Tower Mountain, and Berry Pond,, reputedly the highest pond in Massachusetts. A state campground is located at Berry Pond. From Berry Pond, the trail descends the ridgeline into the village of Hancock, Massachusetts, then ascends the second ridge, which straddles the New York border. Features along this section include Rounds Mountain, Misery Mountain, Berlin Mountain, Mount Raimer, White Rock, and a crevasse called the Snow Hole where ice has been known to persist year round. The trail utilizes conservation land and easements including the Taconic Ridge State Forest and Hopkins Memorial Forest, owned and managed by Williams College. The trail is marked with blue squares containing white blazes throughout its length. All NYSDEC portions of the trail are also posted with blue DEC markers. The trail follows a series of high, open summits and ridgeline overlooking the Hudson River Valley to the west. The entirety of the trail is open to hiking, backpacking, snowshoeing, cross-country skiing, and backcountry skiing, and many sections permit mountain biking, horseback riding and snowmobiling as well. Overnight camping is allowed on the trail; a seasonal campground with facilities is located at Berry Pond. The Taconic Crest Trail originally extended from Berry Pond in Pittsfield State Forest to North Pownal, Vermont. In the late 1990s, the Taconic Skyline Trail in Pittsfield State Forest was separated into two parallel trails: one retained the name "Taconic Skyline" and was designated a motorized recreation trail; the other trail was added on to the southern end of the Taconic Crest Trail, extending it by. To the north, in Vermont, the Taconic Crest Trail once extended into North Pownal, but was closed by request of a property owner; the trail terminus was re-routed north to a newly constructed DEC trailhead at NY Route 346 in North Petersburgh, New York. Not visible from the road, the new trailhead shares a driveway with a private residence and with an old, barred forest road, which are visible; box 25, on the south side of 346, marks the trailhead entrance. It is west of the "Entering NY" sign and from the railroad tracks. A NYSDEC access trail, marked yellow, still leads down to the former terminus of the trail, at the old Prosser Hollow trailhead.