New Marlborough, MA
438 acres
Bird Watching Cross-country skiing/Snowshoeing Hunting Mountain Biking Not Permitted Dog Walking Walking/Hiking (Moderate) Picnicking

About Questing

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

What makes Questing a special place?
Located on the flanks of Leffingwell Hill, Questing features 438 acres of transitional hardwood forest, pockets of wetlands, small streams, and vernal pools.

From the parking area, an old woods road follows a pretty stream for about 1/3 mi. to an open field. This 17-acre upland field of native wildflowers attracts several species of dragonflies and butterflies. Mowed paths follow the edge of the field and connect to a forest loop trail that leads through the woods for about 2/3 mi. around the perimeter of Leffingwell Hill. Look for cellar holes and stone walls, many fascinating in their construction, that tell the story of the 200-year-old settlement known as Leffingwell, where the first non-Native American children were born in New Marlborough. This settlement was abandoned in the late 19th century as farmers migrated to the Midwest.

2 miles of moderate hiking

When to Visit
Open year-round, daily, sunrise to sunset. Allow a minimum of 1½ hours.

Regulations & Advisories

  • To avoid disturbing fragile historical features and ecological communities, please stay on the marked and mowed trails.

  • Seasonal hunting is permitted at this property subject to all state and town laws. Trustees permit is required. Please call 413.213.4751 or email for permit information. Wear bright colors when hiking in the November to December deer hunting season; avoid wearing or carrying anything that is white. Learn more about hunting on Trustees properties.

  • Dogs must be kept on a leash at all times.

  • Mountain biking is not allowed on the property.

The Trustees reserves the right to photograph or video visitors and program participants for promotional use, and usage of our properties implies consent. Find the full policy here.


New Marlborough Hill Road
New Marlborough, MA 01230
Telephone: 413.298.3239

Latitude: 42.1289
Longitude: -73.2508

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.


When to Visit
Open year-round, daily, sunrise to sunset. Allow a minimum of 1 1/2 hours.

Free to all

Property History

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. The first non-Native American children (the Brookins twins) born in New Marlborough were born in that Fort. The land was entirely cleared of most of its trees during subsequent settlement. In the mid 1800s, two brothers, William and Jerome Leffingwell, farmed this property. However, both were killed in farming accidents, and the family emigrated to the midwest. A series of owners left the farmstead abandoned and finally out of business in the early 1900s, when most of the current trees first began to grow. Ruins of the old Leffingwell farmstead house and barn can be found on the reservation.

Robert Lehman was a noted pharmacologist and developer of important drugs for the treatment of heart failure, glaucoma, and other diseases. He was introduced to New Marlborough by his wife Jane, a lifelong resident. Devoted to country life, the Lehmans pursued their passionate hobbies in science and botany, photography, music and literature. The name “Questing,” originates from a mythical beast called the "Questing" in the King Arthur tales, a favorite of Mrs. Lehman. Freda and Sydney Schreiber, lifetime friends of the Lehmans, wrote: "The Lehmans’ quest was to restore to life the dormant, tumbledown farmhouse they purchased more than 50 years ago – which they did, personally, over many years." Part of the quest, also, was to purchase land surrounding the house, as it came available, to keep in the wild. After serious reflection, Robert Lehman chose The Trustees of Reservations to help him do that.

Property Acquisition History
Gift by bequest, with endowment, of Dr. Robert A. Lehman in 1996. Added to an earlier gift of land in 1992 from Richard W. Sellew.

Conservation and Stewardship

Management Planning for Our Properties

Since 1891, The Trustees of Reservations have worked to protect special places in Massachusetts and maintain them to the highest standards. To ensure these standards are met, a program of careful planning and sound management is essential. Comprehensive property management plans are created for each reservation and are completely updated approximately every ten years. We often work with volunteers, property users, and members of the community to carry out this planning, which typically involves several steps:

  • Describing in detail the site’s natural, scenic, and historical resources; identifying management issues related to the protection of those resources. 

  • Describing how visitors use the property; outlining the opportunities that the property provides for people to become involved in the work of conservation and caring for their community.

  • Developing a detailed list of management recommendations, a work plan, and a description of financial needs for implementing the actions.

  • Developing a prescribed routine management program for the reservation that will guide staff work plans, volunteer involvement, and the allocation of human and financial resources.

Maps and Resources

A printed trail map is available for free at the bulletin board in the parking area. Please understand that supplies sometimes run out. We recommend that you download a trail map before you visit. 

Planning Your Visit

Before You Go
We encourage you to visit as many Trustees properties as you can.

Wherever your travels take you, please observe all posted regulations, follow special instructions from property staff, and keep in mind the Stewardship Code:

  • Protect wildlife and plants.
  • Guard against all risk of fire.
  • Help keep air and water clean.
  • Carry out what you carry in.
  • Use marked footpaths and bridle paths.
  • Leave livestock, crops, and machinery alone.
  • Respect the privacy of neighboring land.
  • Enjoy and share the landscape with others.

Click on links below for further visitor information:

Before Setting Out

Enjoying Trustees Reservations


About Hunting on Trustees of Reservations Land