About as far north as you can get in Berkshire County you’ll find Pine Cobble and a beautiful stretch of trail maintained by the Williams College Outing Club. With a moderately steep ascent to one of the best views in the Berkshires, the trail to the 1,894-foot summit winds 1.6 miles through hardwood forests. Although first quarter mile from the trailhead on Pine Cobble Road takes you along the backyards of a neighborhood, you’ll quickly part ways with civilization en route to a knobby, rocky outcrop with valley views of North Adams and Williamstown below, and a snow-capped Mt. Greylock to the south. If you’re looking for a more extended adventure, use the Pine Cobble Trail to access the Appalachian Trail, which is only 2.1 miles from the trailhead.
With over a foot of snow currently on the ground well in place, and more on the way, you should be prepared with snowshoes and hiking crampons, or at a minimum, microspikes, ice cleats, or some form of winter traction. Okay, let’s get hiking!