The Trustees of Reservations Questing Reservation

New Marlborough Hill Road, New Marlborough, MA

About Questing Reservation

The Questing Reservation, commonly referred to as Questing, is a 438-acre property managed by the Trustees of Reservations. The reservation's most prominent feature is Leffingwell Hill, where the remains of a 200-year-old colonial settlement rest. A half-mile out-and-back trail leads from the trailhead to the Leffingwell Loop, which is a little over a mile. On this trail, hikers pass by cellar holes and stone walls that offer a glimpse into 18^th-century colonial times. According to verbal history, a log-and-stone fort on the property was where the first non-Native American children were born in the Berkshires. However, the exact location of this fort is unknown. The settlement grew into the 1800s before eventually being abandoned by the end of the century as many settlers left Western Massachusetts and moved west.

From the trailhead, a 250-foot climb through the forest along an old dirt road leads to the Leffingwell Loop. These woods contain a variety of trees that harbor a diverse bird and animal population, making birding and wildlife viewing common at Questing. Notable birds include golden-crowned kinglets, warblers, nuthatches, and bluejays. Leffingwell Hill is mostly an open meadow, which attracts butterflies in the summer and offers serene sights of the surrounding forestry. The Leffingwell Loop walks right through the thick of this field, immersing visitors in the peaceful nature that encompasses a well-preserved meadow. The forest glows in red, yellow, and orange in the fall, making the Leffingwell Loop excellent for viewing fall foliage. Snowshoeing and cross-country skiing are popular activities at Questing when the snow falls.

The reserve can be accessed from the trailhead on New Marlborough Hill Road, where a free parking lot is available for a small number of cars. Hunting is permitted with written permission, as required by town law.