Rupert is a town located in Bennington County, of the Manchester-Bennington region of Vermont. Historians agree that the town was probably named for Prince Rupert of the Rhine, even though he had been dead nearly 80 years by the time of the Grants, because he was a national hero beloved by all Englishmen.

One of Rupert's first settlers was Reuben Harmon, a metalsmith, who was given the right to mint coins, called "Vermont coppers," for the Republic of Vermont. The coins were first struck in 1785 and continued to be minted until Vermont's admission to the United States in 1791 as the State of Vermont.

Some notable people of the area include: Frederick Buechner, writer & theologian; and Israel Smith, lawyer, politician, & fourth Governor of Vermont.