Readsboro is a town located on Route 100 in the southeastern corner of Bennington County, in the Manchester-Bennington region of Vermont. The area's terrain is quite mountainous, with over a dozen peaks rising to over 2,500 feet, most of which are unnamed.

The town, originally called Readesborough, was named for landholder John Reade. In some early records, some residents stated that they lived in Reedsberry.

Some notable people of the area include: Throope Chapman, one of the Readsboro founders; Welcome Chapman, early Mormon leader, grandson of Throope Chapman; and Wayne Winterrowd (1941–2010), a horticulturist & author known for his lush gardens in Southern Vermont.