Leffingwell Loop

The Leffingwell Loop begins from the small parking area off New Marlborough Hill Road in New Marlborough, MA. From the lot, follow a woods road for a short distance to reach an open meadow, where the route transitions into a forested loop around Leffingwell Hill. From the edge of the field, hikers can continue in either direction to complete the loop through mixed hardwood forest and wetlands. Managed by The Trustees of Reservations, the route passes cellar holes, stone walls, and other remnants of the former Leffingwell homestead—features that hint at the area's early colonial history. Stay on marked or mowed paths to avoid damaging fragile historic and ecological features. The high meadow atop the hill offers seasonal wildflowers and active insect life, with good opportunities for birding and wildlife observation throughout the surrounding forest. Snowshoeing and cross-country skiing are permitted in winter, though the parking area is not plowed. Dogs are allowed on leash. Hunting is allowed in season with local permission—wear bright orange in fall. This is a rewarding route for a moderate day hike in the southern Berkshires.