At the heart of the property is a 1.5-mile trail network. The main trail starts from a new parking area on Cunningham Pond Road near the intersection with East Mountain Road, from there traversing through woodlands and a hemlock grove before crossing a stream and climbing to a large open field with sweeping views of Pack Monadnock and Temple Mountain. Along the trail, you can find trees with woodpecker holes, mushrooms, and moss-covered rocks amidst the sounds of the stream and birds flitting above.

From the field, a spur trail winds down to an old carriage road at the water’s edge. Another spur trail, branching off closer to the main trail’s beginning, connects you to the Goyette Natural Area, another Conservancy property, off East Mountain Road.

The Cunningham Pond Trails were laid out by Rick Brackett, land manager for the Monadnock Conservancy, and Lew Shelley of SnowHawk LLC, an independent trail design and construction firm. Most of the labor to build the trails was supplied by teams of young volunteers from the Student Conservation Association. In the fall of 2019, two teams spent one week each cutting brush, clearing duff, tamping soil, and building two rustic timber bridges to create a safe, scenic walking path.