About Vail Farm LLC
Historic Family Farm in Bennington, VT Since 1803
Vail Farm LLC is an eight-generation family farm rooted in Bennington, Vermont, with a history that spans more than two hundred years.
The farm’s origins trace back to 1813, when John Vail purchased approximately 150 acres along what is now Vail Road, establishing what would become one of the area’s enduring agricultural homesteads. For generations, the farm has remained part of the same family landscape, continuing a legacy of stewardship, resilience, and community connection.
The historic Vail Homestead stands as a testament to that legacy. Built in the early 19th century, the Federal-style farmhouse and surrounding agricultural landscape reflect the evolution of farming in Bennington through changing economic and environmental conditions.
A Farm That Evolved With the Times
Over the course of its history, Vail Farm has adapted to meet the needs of each era.
The land was first shaped through early livestock and agricultural production, including sheep farming, which remained central to the farm until the 1840s. As markets changed, the farm transitioned into dairying, cattle, and horse farming, reflecting the agricultural economy of the region.
The soil and surrounding landscape of southwestern Vermont made the property especially suited for grass crops, hay, oats, buckwheat, fruit trees, and livestock production. For more than two centuries, the farm has evolved in response to changing markets while remaining grounded in the land itself.
Historic outbuildings, tools, and agricultural structures throughout the property continue to tell that story.
A Living Family Legacy
Vail Farm has remained active through generations of the Vail family and continues today through the Cooke family.
From greenhouses operated between 1988 and 2008, offering annuals, vegetables, herbs, perennials, trees, shrubs, sweet corn, pumpkins, and landscape design, to the farm’s current operations, the property has remained a working agricultural space deeply connected to the Bennington community.
Growing up on the farm, the next generation learned the work firsthand — from greenhouse operations and customer service to harvesting crops directly from the field.
That hands-on experience, combined with Jesse’s formal education in sustainable horticulture from the Stockbridge School of Agriculture at UMass Amherst, continues to shape the farm’s present direction.
Rooted in Community
For over two centuries, Vail Farm has been part of the landscape and story of Bennington.
Travelers along Vail Road still experience much of the same agricultural setting that has defined this property since the early 1800s. The homestead remains a symbol of Bennington’s farming heritage and the enduring value of family-operated agriculture.
As the farm continues to grow and evolve, its foundation remains the same: land, family, and community.
