Featherstone was born in Worcester, Massachusetts, in 1936 and grew up in nearby Berlin. After graduating from the Worcester Art Museum's art school, in 1957, he was offered a job designing three-dimensional animals for Union Products, Inc. Over his years at Union Products, Featherstone sculpted over 750 different items, the first two of which were a girl with a water can and a boy with a dog.
Featherstone's early career involved designing 3D animal figures for Union Products, Inc., after graduating from the Worcester Art Museum's art school in 1957. He created over 750 distinct items during his tenure at the company, with his initial creations being a girl holding a water can and a boy with a dog.