Visit a landscape of returning forest, wetlands, remnant cellar holes, and stone walls that recall a long-abandoned settlement dating to early Colonial times.
Located on the flanks of Leffingwell Hill, Questing features extensive tracts of transitional hardwood forest, pockets of wetlands, small streams, and vernal pools. This 17-acre upland field of native wildflowers attracts a variety of dragonflies and butterflies. A mowed path along the field edge connects to a forest loop trail that leads through the woods for two-thirds of a mile around the perimeter of Leffingwell Hill, a 200-year-old settlement where the first non-Native American children were born in New Marlborough.
From the parking area, trace an old woods road along a pretty stream for a third of a mile to an open field. Look for cellar holes and stone walls—many of which evince fascinating construction—across two miles of trails.
FREE to all.
While the property is open in the winter, please note that we do not plow the parking lot.
New Marlborough Hill Road
New Marlborough, MA 01230
From intersection of Rts. 23 and 57 in Monterey, take Rt. 57 East for 5 mi. Turn right onto New Marlborough Hill Rd. and follow for 0.6 mi. to entrance and parking (8 cars) on left.
We recommend that you take a photo of the map on your phone so you can refer to it during your visit, or download a trail map before you visit.
The Trustees Hiking Challenge: With over 100 places and hundreds of miles of trails to explore, join our free challenge to get you hiking and exploring M...
Seeking, protecting, and caring for Massachusetts’ most special places
When you give land to The Trustees, you are creating a permanent legacy and helping ensure the healthy future of our communities.
For more than a half-century, this country retreat, named “Questing” by its owners, was the cherished summer home of Dr. Robert Lehman and, until her passing in 1978, his wife Jane Fraser Lehman.
Native Americans passed through and may have camped at the property. The New Marlborough Proprietor’s records indicate that the first Fort to store gun powder built by settlers was placed at the highest point of the reservation.
...you are rewarded with beautiful panoramic views of the neighboring hills. The setting us peaceful and pristine.
– BerkshireBaylin, Trip Advisor
Woodlands & Parks
New Marlborough | Berkshires
Wander across more than 200 acres of forest and through a maze of thickets, follo...
Tyringham | Berkshires
Wander through an intimate setting of outdoor sculpture and elegant gardens, nour...