Stern graduated from the University of Pittsburgh in 1947 with a degree in English when the poetry scene in Pittsburgh was mostly non existent. While in college he found a support system through fellow poets Jack Gilbert and Richard Hazley and reading the poetry of Pound, Yeats, Eliot, Marianne Moore, and Cummings. After serving in the army from 1946-1947, Stern, Hazley, and Gilbert traveled to Paris in order to develop their writing skills. It was here that Stern worked on his long poem, Ishmael's Dream. While raising a family Stern taught both high school and college courses in Pennsylvania, New York, New Jersey, and even Scotland. In 1969 The Pineys, a long poem about the people who reside in the Pine Barrens, was published in the Journal of the Rutgers University Library.

“Now, there I was in 1948, in the midst of all this, you see, writing poetry, writing short stories, desperately trying to make – with no real access or information, no community, with no knowledge of how to proceed, with no poetry readings available, with no older poets to come in contact with – my archetypical move into aesthetics. I was going to museums, listening to music, going to talks, reading every book I could read. I made lists for myself. I read till I was blind, night and day, awakening and discovering in myself – with almost a kind of luxury – the joy of aesthetics, the joy of beauty, and all the complexity that lay therein.” 

–Interview with Stern by Leslia Klein for Boulevard, 1992.