Winchester began his dance training at Philippine High School for the Arts and took BA Anthropology at the University of the Philippines, Diliman. He was a lead dancer of the UP Filipiniana Dance Group and became the Associate Artistic Director in 2011.
He joined the premier jazz and contemporary dance company in the Philippines and performed locally, in the US, Europe, and Southeast Asia. He was one of the ensemble members in Repertory Philippines’ Song and Dance. He performed in various Royal Caribbean International production shows as a cast dancer and aerialist. He was part of the Miss Saigon UK International Tour and Miss Saigon Danish version in Copenhagen, Denmark. In 2022, Chester was the Dance Captain of the Miss Saigon German version in Vienna, Austria.