New Marlborough

438 acres

Visit a landscape of returning forest, wetlands, remnant cellar holes, and stone walls that recall a long-abandoned settlement dating to early Colonial times.


Plan Your Visit
  • Overview
  • Ideas for Your Visit
  • Admission & Hours
  • Directions & Contact Info
  • Property Map
  • Regulations & Advisories


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.

Ideas for Your Visit

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.

Admission & Hours

FREE to all.

While the property is open in the winter, please note that we do not plow the parking lot.

Directions & Contact Info

New Marlborough Hill Road
New Marlborough, MA 01230


Get directions on Google Maps.

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.



Property Map

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.

Regulations & Advisories

  • To avoid disturbing fragile historical features and ecological communities, please stay on the marked and mowed trails.
  • Hunting is permitted at this property subject to all state and town laws. Carried written permission is required per town bylaw; please contact for permission. It is recommended to wear brightly colored clothing like an orange vest or hat during the hunting season. Hunting is not allowed on Sundays. Learn more about hunting on Trustees properties, and read safety tips for non-hunters.
  • Dogs must be kept on a leash at all times.
  • Mountain biking is not allowed on the property.
  • While the property is open in the winter, note that we do not plow the parking lot.
  • PHOTOGRAPHY: We ask that photographers or their clients become Supporting Level Members before conducting portrait sessions at this property.  Click here for more information, and to request permission for any portrait sessions. The Trustees of Reservations reserves the right, and may give permission to its designated photographers and videographers, or to outside media, to photograph or video visitors and program participants at all its facilities and properties.
Before Setting Out
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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.

Learn more
The View From Here
See What People Say are rewarded with beautiful panoramic views of the neighboring hills. The setting us peaceful and pristine.

BerkshireBaylin, Trip Advisor

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