The town of Pittsfield is known as the heart of the Berkshires and serves as the hub for several of the best snowmobile trails Massachusetts has to offer. The 12,000-acre Beartown State Forest turns into a winter wilderness wonderland when the snow flies, with spectacular views and over 25 miles of snowmobiling trails. Keep an eye open for deer, bear, bobcat, fisher and other wildlife, though the park’s namesake, the Black Bear, hibernates in winter. The October Mountain State Forest provides some prime snowmobiling on its 16,500 acres, as does the Pittsfield State Forest, with over 11,000 acres of mature woods, including Berry Pond, one of the highest natural bodies of water in the state at 2,150 feet in elevation.

The Mount Greylock State Reservation features Mount Greylock, the highest natural point in Massachusetts at 3,489 feet above sea level, which offers spectacular views to five states. During the winter, the roads are closed to automobiles, providing snowmobilers with over 70 miles of the best snowmobile trails in the state, beautiful and picturesque, including a 12-mile section of the Appalachian National Scenic trail. Tolland State Forest has around 15 miles of snowmobile trails near the Otis Reservoir, the centerpiece of the forest. The Monroe State Forest is known for its deep valleys, steep mountains and tall trees making it a winter joyland for snowmobile riders. The 1,158 acres of the Jug End State Reservation provides those that want to ride snowmobile with some of the most scenic areas in the Berkshires, plus offers access to the Appalachian Trail.