Historically, Rupert has had a land-based economy. In the 1860’s over 90% of local residents were farmers, but the town also had 4 stores, 3 sawmills and several manufacturing and repair establishments. There were also cheese and butter plants to process locally produced dairy products, which were shipped by rail to regional markets. Today, Rupert is largely a bedroom community for people who live in town and work elsewhere.

As of 2012 the resident work force was estimated at about 350, down some 3% since 2000. About 2/3 of this number was employed in the private sector, mostly in the service sector, with over 25% being self-employed. An estimated 30% worked in town, 44% worked elsewhere in Bennington County and only 5% traveled out of state.

The Economic Goal, according to the Town Plan is  “To accommodate and support business development that offers well paying jobs and needed goods and services for local residents and is compatible with, and enhances, the town’s rural and small town character.”

Businesses in Rupert

American Country Rugs

Authentic Designs  Original and Historic Reproduction Lighting Made in Vermont

Axel Blomberg’s Maple Syrup (802) 394-7897

Baker’s Burner Service Plumbing and Heating (802) 394-7816

Black Rose Creamery Artisanal Goat Cheese

Ceglowski and Thrasher Attorneys at Law

Country Gallery Antiques

Flour Girl Bake Shop Sweets and Treats

Hectic Electric (802) 394-2443


Jane Davies Studios

Lourie’s Caretaking (802) 394-7898

MDC Construction (802) 394-2439

Mountain Valley Maple Farm (802) 394-2928

Power to Move Excavating (802) 394-2445

Renovations and Home Repairs by Jay (802) 430-2456

Rupert Mechanical Services (RMS) Plumbing and Heating

Rug Crazy

Rupert Rising Breads

Rupert Valley Holsteins

Sherman’s Store (802) 394-7820

Twin Brooks Maple Farm