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A 270-acre, family-owned farm in Rupert, Vermont, where animals, people, and nature thrive together.
Sterling Hollow Farm is a one-of-a-kind property nestled in the hills of southern Vermont. With wide-open pastures, renovated cattle/horse barns, and blooming natural ponds, we’ve created a space that honors the land and the animals who live here.
Owned and operated by Michele and Jim O’Brien, the farm spans over 270 acres and includes equine facilities, heritage breed cattle, goats, ducks, chickens, a vineyard-in-progress, and more. Every square foot is part of our ongoing effort to build something restorative, sustainable, beautiful, and deeply personal.
Each part of the farm is a reflection of our values—care, connection, and conservation.
Equine Facility
With a new outdoor arena, access to the D&H Rail Trail, horse boarding, open pastures, and future clinics.
Randall Cattle
A rare heritage breed being revived and reestablished in Vermont, known for their historical significance.
Vineyard
A newly established grape vineyard on 20 acres of land, using both red and white grapes.
Join us on our farming journey!
Connect With Us
Whether you’re looking to board a horse, explore the trails, volunteer on a working farm, or simply stay in the loop with what we’re building, we invite you to get in touch.
Farm-Proud Goods
Show your support with limited-run hats, tees, and gear designed right here on the farm. Soft, simple, and farm-tested—our swag is a great way to represent Sterling Hollow Farm.
