The Trustees of Reservations: Questing

During my trip to the Berkshires in July 2023, I took a hike at Questing, a seventeen-acre property owned by The Trustees of Reservations. I visited several other properties owned by the Trustees during this trip, including Ashintully Gardens, Tyringham Cobble, and Mission House. Like these other properties, this park had its own unique history.

The trails of Questing go up and around Leffingwell Hill, named after brothers William and Jerome Leffingwell who built a farm on the property and brought their families to live with them. Both brothers died in horrific farming accidents. In 1873 at age fifty-two, William was kicked to death by a horse, leaving his wife with eleven children. In 1879 at age forty-eight, Jerome was crushed by a thirty-foot long timber at a barn construction site and died several days later. After these accidents, surviving family members abandoned the seemingly cursed property and moved West. Hikers can see the ruins of this farm while on the trails.

Prior to the tragedies of the Leffingwell family, the hill was an important site in the colonial village of New Marlborough. English colonists built a fort at the top of the hill and stored gunpowder, fearing defensive attacks from Native Americans who had lived in the area for thousands of years. According to local tradition, the Brookins twins were the first White children born in the area, but little information on their lives exists outside of the name.

During the 1920s, Dr. Robert Alonzo Lehman and his wife Jane Blair Fraser Lehman were the final private residents of the property. They called their place Questing after the Questing Beast of Arthurian legends. Dr. Lehman was an ophthalmological pharmacologist who invented drugs to improve eye surgery. He had a wide range of interests, which included playing the flute and pipe organ, along with collecting other musical instruments. He donated much of his music collection to the MET in New York City and an 1885 Roosevelt Portable Pipe Organ to MFA Boston. Mrs. Lehman died in 1978 at age 64, while Dr. Lehman died in 1996 and left the property to the Trustees.

Questing is open from dawn to dusk throughout the year and is free to the public. Hunting is permitted during open season. A small parking lot is at the bottom of Leffingwell Hill next to New Marlborough Hill Road. While the meadow is peaceful and filled with wildflowers during the summer, hikers must invest a lot of effort to get there. The trail from the parking lot to the top of the hill is about 2,000 feet long with a 280 foot increase in elevation, or a 14% grade. Because of this steep grade, walking up the hill is strenuous, and walking down the hill can be dangerous especially when wet or without the proper equipment and footwear. The loop around the top of the hill adds another 90 feet in elevation and is overgrown in places. Be sure to adequately prepare for the trip.

Abby Epplett’s Rating System

Experience: 7/10

Accessibility: 3/10