The quiet ruins of Questing, Massachusetts speak volumes about Massachusetts’s dynamic history. Once a place of ambition and daily life, this ghost town now serves as a historical landmark, inviting visitors to imagine the community that once flourished here.
County: Berkshire
Zip Code: Not available
Latitude / Longitude: 42°07′19″N 73°15′06″W / 42.1219°N 73.2518°W / 42.1219
Elevation: Not available
Time Zone: Eastern (EST) (UTC-5)
Established: 1996
Disestablished: Not available
Comments: Research shows that questing is a 438-acre (177 ha) open space preserve and colonial-era historic site located in New Marlborough, Massachusetts within The Berkshires. The property, acquired in 1996 by the land conservation non-profit organization The Trustees of Reservations, is named for a mythical beast from Arthurian Mythology called the Questing Beast.
Remains: The former settlement questing Reservation is on a hill where the first fort was built in the original New Marlborough settlement, and where the first non-Native American children were born, the Brookins twins. The precise location of this site is no longer known. Later this site was also the location of the settlement of the Leffingwell family, abandoned in the Great Depression. The only remains of the Leffingwell farmstead are cellar holes and stone walls.
Current Status: Present-day visitors will find the site is the reservation includes hiking trails, open meadows and hayfields, vernal pools, and streams. It is open to hiking, picnicking, cross country skiing, and hunting (in season). A trailhead is located on New Marlborough Hill Road in New Marlborough. Bikes, snowmobiles, and motorized vehicles are prohibited.
Remarks: Visitors to Questing often reflect on how quickly fortunes could change in frontier communities. The site serves as an important reminder of Massachusetts’s dynamic history and the transient nature of many early settlements.
Questing, Massachusetts stands as a testament to the transient nature of human settlements and the enduring power of the New England landscape. Once a thriving colonial-era settlement and later a 19th-century farming community, Questing now exists primarily as a nature preserve where visitors can explore the remnants of its past while enjoying its natural beauty. The story of this ghost town reflects the changing economic and social patterns that have shaped rural Massachusetts over three centuries.
Origins and Early Settlement
The area now known as Questing was originally part of the territory of the Mohican Native American tribe. European settlement in the region began in the early 18th century when the Massachusetts Bay Colony established a military fort on what later became known as Leffington Hill in New Marlborough. This fort served as protection for colonial settlers against potential attacks during the ongoing conflicts between European powers and their Native American allies.
The fort holds a significant place in local history as the birthplace of the first non-Native American children in the Berkshires—the Brookins twins. This milestone marked the beginning of permanent European settlement in what would eventually become the town of New Marlborough, with the Questing area representing one of its earliest settled districts.
Following the conclusion of the French and Indian War in 1763, the military threat diminished, and the fort’s importance waned. The surrounding area gradually transitioned from a military outpost to an agricultural settlement as more families moved into the region, attracted by the available land and the opportunity to establish farms in the fertile valleys between the Berkshire hills.
The Leffingwell Era
The most well-documented period in Questing’s history began in the mid-19th century when two brothers, William and Jerome Leffingwell, established a substantial farm on Leffington Hill. The hill itself was likely named after the family, who became prominent landowners in the area. The Leffingwells developed a productive agricultural operation that became the center of a small community.
Life on the Leffingwell farmstead exemplified the challenges and rewards of rural New England farming during this period. The brothers and their families cultivated crops suited to the region’s short growing season and raised livestock that could withstand the harsh Berkshire winters. Their farm represented the economic backbone of the small Questing settlement, providing employment and serving as a hub for local trade and social activities.
Tragedy struck the Leffingwell family when both brothers died in separate farming accidents. These deaths dealt a severe blow to the community’s stability and prosperity. Without the leadership and labor of the Leffingwell brothers, the remaining family members struggled to maintain the farm. Eventually, they made the difficult decision to abandon their homestead and relocate to the Midwest, where agricultural opportunities seemed more promising and less dangerous.
The departure of the Leffingwell family marked the beginning of Questing’s decline. Their farmstead changed ownership multiple times over the following decades, but none of the subsequent owners achieved the same level of success or community leadership that the Leffingwells had provided.
Decline and Abandonment
The late 19th century brought significant challenges to small farming communities throughout New England, and Questing was no exception. The industrial revolution drew younger generations away from agricultural life and toward manufacturing jobs in growing urban centers. Simultaneously, the opening of the American West, with its vast expanses of fertile land, made the rocky, hilly farms of New England less economically competitive.
These broader economic and demographic trends accelerated Questing’s decline. By the early 1900s, the Leffingwell farmstead had been abandoned entirely, along with most of the surrounding properties that had once formed the small community. The buildings, no longer maintained, began to deteriorate under the harsh New England weather conditions.
The economic depression of the late 19th century, which hit rural areas particularly hard, contributed to the final exodus from Questing. The remaining families left the hilltop and either relocated to more prosperous regions of New England or joined the westward migration that was transforming the American landscape. As they departed, they left behind their homes, barns, and the stone walls that had marked field boundaries and property lines for generations.
Nature began to reclaim the abandoned settlement. Forests that had been cleared for agriculture gradually returned, enveloping the remnants of human habitation. The wooden structures rotted and collapsed, leaving only their stone foundations and cellar holes as evidence of the community that had once thrived there.
Rebirth as “Questing”
For much of the 20th century, the abandoned settlement remained largely forgotten, known primarily to local residents and historians interested in New Marlborough’s past. The land changed hands occasionally but saw little development or use beyond limited logging and hunting.
A new chapter in the area’s history began in the 1970s when Dr. Robert Lehman, a noted pharmacologist, purchased the old Leffingwell farmstead and surrounding land. Lehman was drawn to the property’s natural beauty and historical significance. He named his country retreat “Questing” after a mythical beast from Arthurian legend—the Questing Beast, a creature that was perpetually sought but never caught. This name reflected both Lehman’s appreciation for medieval literature and perhaps his own quest for a peaceful retreat from his professional life.
Dr. Lehman and his wife Jane Fraser used Questing as a summer home, appreciating its seclusion and the rich natural environment. While they did not attempt to rebuild the historic structures, they maintained the property and developed a deep connection to the land and its history. Their stewardship helped preserve what remained of the old settlement while allowing the natural ecosystem to flourish.
In 1996, demonstrating remarkable generosity and environmental consciousness, Lehman donated the entire 438-acre property to The Trustees of Reservations, a Massachusetts conservation organization. This donation ensured that Questing would be permanently protected from development and would remain accessible to the public as a nature reserve.
Questing Reservation Today
Today, Questing exists as the Questing Reservation, a protected natural area that preserves both ecological and historical resources. The reservation encompasses 438 acres of diverse habitats, including hardwood forests, wetlands, and a 17-acre field of native wildflowers that provides important habitat for pollinators and other wildlife.
Visitors to Questing Reservation can explore a network of walking trails that wind through the property, offering opportunities to experience its natural beauty and encounter its historical features. The most visible remnants of the former settlement are the cellar holes of the farmhouse, the ruins of the barn, and numerous stone walls that crisscross the landscape. These stone walls, built by hand from rocks cleared from fields, represent countless hours of labor by the area’s early settlers and stand as enduring monuments to their determination and industry.
The reservation is managed with a dual focus on ecological conservation and historical preservation. The Trustees of Reservations maintain the trails and interpretive materials that help visitors understand both the natural and human history of the site. They also work to protect the native plant and animal species that now inhabit the former farmland, creating a balance between honoring the human past and nurturing the natural present.
Questing Reservation has become a popular destination for hikers, nature enthusiasts, and history buffs. Its relatively remote location in the southern Berkshires helps maintain the sense of discovery and exploration that its name suggests. Visitors often report a powerful sense of connection to the past when standing amid the stone ruins and imagining the lives of those who built them.
Historical and Cultural Significance
Questing’s historical significance extends beyond its role as a typical New England farming community. The early military fort established on Leffington Hill represents an important chapter in colonial history, particularly in understanding the European settlement of western Massachusetts and the complex relationships between colonists and Native Americans.
The birth of the Brookins twins at the fort—recognized as the first non-Native American children born in the Berkshires—symbolizes the beginning of permanent European settlement in the region. This milestone marks a significant transition point in the area’s demographic and cultural history.
The Leffingwell farm’s rise and fall illustrates broader patterns in New England’s agricultural history. The challenges faced by the Leffingwells and their neighbors—harsh weather, difficult terrain, economic pressures, and the lure of better opportunities elsewhere—were common factors in the abandonment of many hill farms throughout the region during the 19th century.
The stone walls that remain at Questing are particularly significant as cultural artifacts. These walls, constructed without mortar using stones cleared from fields, represent a distinctive feature of the New England landscape. They serve as physical evidence of the immense labor invested by early settlers in transforming forested land into productive farms. The patterns of these walls also reveal information about historical property boundaries, land use practices, and agricultural techniques.
Dr. Lehman’s decision to donate the property to The Trustees of Reservations reflects a more recent but equally important aspect of New England’s cultural history—the conservation ethic that has helped preserve significant natural and historical landscapes throughout the region. This act of philanthropy ensured that Questing would remain undeveloped and accessible to the public, allowing future generations to connect with both its natural and human history.
Questing in Context: Ghost Towns of Massachusetts
Questing represents one type of ghost town found in Massachusetts—a rural settlement abandoned primarily due to economic changes and demographic shifts rather than a single catastrophic event. Unlike the Swift River Valley towns (Dana, Enfield, Greenwich, and Prescott) that were deliberately flooded to create the Quabbin Reservoir, or mining communities like Davis that collapsed when their economic reason for existence disappeared, Questing faded gradually as agriculture became less viable in the region.
This pattern of rural abandonment was common throughout New England in the late 19th and early 20th centuries. As industrialization transformed the American economy, many farming communities, particularly those in hilly, rocky areas with short growing seasons, could not compete with more productive agricultural regions. Young people left for factory jobs in cities or for better farming opportunities in the Midwest, leading to the gradual depopulation of many rural areas.
What distinguishes Questing from many other abandoned settlements is its successful transformation into a protected natural area that honors its human history while creating new value as an ecological preserve. While the community itself has vanished, the landscape continues to tell its story to visitors who explore the reservation’s trails and encounter the physical remnants of its past.
Visiting Questing Today
For those interested in experiencing this ghost town firsthand, Questing Reservation is open to the public year-round from sunrise to sunset. The property is located on Questing Road in New Marlborough, Massachusetts, in the southern Berkshires. Visitors can park in a small lot at the entrance and access several miles of marked trails that lead through the property.
The main trail loop passes by the most significant historical features, including the cellar holes of the Leffingwell farmstead and numerous stone walls. Interpretive signs provide context for these remnants, helping visitors understand what they’re seeing and imagine the community that once existed there.
Spring and early summer offer opportunities to see the wildflower meadow in bloom, while fall brings spectacular foliage colors to the hardwood forests. Winter visits, while challenging due to snow and cold, provide a different perspective on the landscape and make the stone walls and cellar holes more visible without summer vegetation.
Visitors should come prepared for a rustic experience—there are no facilities at the reservation, and the trails can be muddy or overgrown in places. Good hiking shoes, water, and insect repellent (in warm months) are recommended. The relatively remote location and limited signage contribute to the sense of discovery that makes Questing a unique destination for those interested in Massachusetts ghost towns.
Legacy and Lessons
The story of Questing offers several important lessons about human settlement, economic change, and our relationship with the natural environment. It demonstrates how communities can rise and fall in response to broader economic and social forces, and how the landscape itself can both shape human activity and be shaped by it.
The abandoned cellar holes and stone walls of Questing remind us of the impermanence of human constructions and the resilience of the natural world. The forests that have reclaimed former fields and pastures illustrate the dynamic relationship between human activity and natural processes.
At the same time, Questing’s transformation into a protected reservation shows how abandoned places can find new purpose and value. What was once a site of agricultural production and community life has become a space for conservation, recreation, and historical education—serving new generations in ways its original inhabitants could never have imagined.
In this way, Questing is not merely a ghost town—a place defined by absence and loss—but also a living landscape that continues to evolve and create new connections between people and place. Its story is not simply one of abandonment but also of renewal and rediscovery, making it a particularly fascinating example among Massachusetts’ ghost towns.
Sources:
1. History of Massachusetts Blog. “Ghost Towns in Massachusetts.” https://historyofmassachusetts.org/ghost-towns-massachusetts/
2. The Trustees of Reservations. “Questing History.” http://thetrustees.org/content/questing-history/
3. Wikipedia. “Questing (New Marlborough, Massachusetts).” https://en.wikipedia.org/wiki/Questing_(New_Marlborough,_Massachusetts)
4. The Trustees of Reservations. “Questing, New Marlborough, MA.” https://thetrustees.org/place/questing/
5. Housatonic Heritage. “Questing Reservation – New Marlborough, MA.” https://housatonicheritage.org/places/questing-reservation-new-marlborough-mass/
6. Berkshires Outside. “Questing Reservation in New Marlborough, MA.” https://berkshiresoutside.org/place/questing-reservation-new-marlborough-ma/
7. Western Mass Hilltownhikers. “Questing in New Marlborough.” https://westernmasshilltownhikers.com/2024/03/04/questing-in-new-marlborough/