Rupert blends rolling farmland, forested hills, and clear Batten Kill headwaters into a setting that rewards both quiet routines and weekend adventure. Tucked in Bennington County with easy access to the shops and dining of Manchester and the arts scene in Dorset, the town offers a peaceful pace without feeling remote.
Outdoor time is a way of life here. Hike, ski, or snowshoe among working fields and 30+ miles of trails at the nonprofit Merck Forest & Farmland Center, a local gem with year-round programs for all ages. History buffs and garden lovers find inspiration at Hildene, The Lincoln Family Home. Summer brings theater under the stars at the Dorset Theatre Festival, while Bromley Mountain adds lift-served fun in every season. On hot days, families head to Lake St. Catherine State Park for swimming, paddling, and picnics.
Families appreciate strong local schooling. Younger students attend Mettawee Community School in nearby Pawlet. For grades 7–12, Rupert is a school-choice town, and many teens commute to respected options such as Burr and Burton Academy or Long Trail School.
Whether you’re seeking acreage, a historic farmhouse, or a low-maintenance retreat close to trails and trout water, Rupert delivers small-town ease with notable amenities close by. Moving in or moving on, Agent Pronto can connect you with a top real estate professional to guide your sale or purchase.
Merck Forest & Farmland Center • Hildene, The Lincoln Family Home • Dorset Theatre Festival • Bromley Mountain • Lake St. Catherine State Park • Mettawee Community School • Burr and Burton Academy • Long Trail School