Rupert is a small farm village in the Taconic Mountains
In Southwestern Vermont on the border of Upstate New York, Rupert offers rural living in the Taconic Mountains. “It’s a real classic Vermont scene—a little farm village cultivated by all the land around it,” says Scott McChesney, principal broker of McChesney Real Estate, who has worked in the region for more than 40 years. Farms, rolling hills and forested mountains exhibit the natural beauty of Rupert, where a tiny village center captures the small-town atmosphere with a general store, post office and a few churches. There are also a number of historic buildings, including former schoolhouses now used as a library and for the local historical society, and an early 19th-century farmhouse called Carver House that was used to film the first 10 seasons of the PBS television show Cook’s Country.
Historic and modern houses with scenic views
Some houses are tucked away in the woods, while others back up to rolling farmland or sit on hillsides with mountain views. Properties date anywhere from the early 1800s through the 2000s and can have anywhere from 1 acre to hundreds of acres of land. In recent years, historic Colonials and midcentury Cape Cods have sold for $350,000 to $380,000. Large farmhouses and contemporary homes with 10 to 70 acres of land range from around $400,000 to $600,000. According to McChesney, upscale houses on hundreds of acres in the mountains near Dorset have sold for more than $2 million.
A rail trail by the Indian River and nature programs at Merck Forest & Farmland Center
The Delaware and Hudson Rail-Trail runs for nearly 20 miles along the Indian River. “It’s nice because it’s not a very busy trail,” says McChesney. “People use it for hiking, riding bikes and horseback riding. It also crisscrosses with the river, so it’s easy to find a fishing hole.” Merck Forest & Farmland Center is a private organization all about providing outdoor experiences and educational opportunities. The 3,500-acre property is open to the public and often a location for school field trips. The forest features 30 miles of nature trails with mountain overlooks. The farm offers seasonal activities such as maple sugaring demonstrations, berry picking and learning about the farm-to-table process.
Sherman's Store selling local products since the 1850s
The village center along Rupert Road is a very rural area with farms situated between the town’s general store, churches and volunteer fire department. Sherman's Store has been serving the community since the 1850s. It sells grocery items, including locally made products, such as Battenkill Creamery milk, Green Mountain Coffee and Vermont maple syrup. The general store also serves sandwiches daily, pizza on Friday nights and breakfast on Sunday mornings. More retailers and grocery stores are 10 minutes away in Dorset and 20 minutes in Manchester.
Community gatherings through Rupert Village Trust
Rupert Village Trust has made it a point to find various ways to keep the community connected. Set up in the historic Sheldon General Store, the non-profit organization has a café and hosts various social gatherings throughout the week. “Rupert Village Trust is a wonderful group of people,” says McChesney. “They have coffee hour on Saturday mornings, open mic nights, game nights, and a lot of people turn out.”
A school choice program with options in New York
Students are served by The Mettawee School District, part of the Bennington-Rutland Supervisory Union. Kindergarten through sixth-grade students attend Mettawee Community School, which receives a C grade from Niche. Students in seventh through twelfth grade can choose where they want to finish their education, including schools in New York. One option could be attending the combined middle and high school at Salem Washington Academy in Salem, New York, which receives a B-minus.
Getting around Rupert and to other nearby towns
Vermont routes 30, 153 and 315 are used to get around town and to other nearby communities, such as Dorset and Manchester. The closest hospital is Rutland Regional Medical Center, about 35 miles away in Rutland, Vermont. Travelers can drive 60 miles to fly out of Albany International Airport.
Written By
Nicolas Stuart
