The trail extends from U.S. Route 20 in Hancock, Massachusetts, less than 1 mi (1.6 km) east of the New York border, north along the ridgecrest of the Taconic Range within Pittsfield State Forest and officially ending at Brodie Mountain Road on the Hancock/ Lanesborough town line.
Originally built as a hiking trail, the Taconic Skyline Trail sees heavy use by all-terrain vehicles and snowmobiles and is now officially maintained for primarily motorized use.
Recent grants through the Massachusetts DCR's Commonwealth Connections project have provided 40,000 dollars to ATV clubs for trail surface rehabilitation.
The Taconic Skyline Trail was blazed in the 1930s by the Civilian Conservation Corps as a hiking trail, 25 miles (40 km) long, extending from Massachusetts Route 41 in Richmond to the northern end of Brodie Mountain in Williamstown.
Features along the trail include the highland Cranberry Pond and Twin Ponds, Doll Mountain, Smith Mountain, Tower Mountain, Berry Pond, 2,150 feet (660 m) (reputed the highest pond in Massachusetts), Poppy Mountain, Jiminy Peak, and Widow White's Peak.