Alloway and Sylvia Sleigh arrived in New York on the Rotterdam on September 9, 1961. It was sweltering, and they were taken for dinner at the air-conditioned Pen and Pencil restaurant by Barnett and Annalee Newman, then went on to Birdland to hear Ornette Coleman, to whom they were introduced at the end of his set. That night they stayed at Betty Parsons’ apartment on 68th Street. New York must have seemed everything Alloway hoped for.

Alloway had been offered a year's teaching job at Bennington College in Vermont by E.C. (Gene) Goossen, then head of Art, soon after he visited the college in 1958 with Betty Parsons. He had initially rejected the offer, partly because of his commitment to London Situation, and partly because Sylvia Sleigh thought he should finish his two books on American painting. Goossen and Parsons phoned him to say his rejection was “mad” because of the opportunity it provided him, and Alloway reconsidered and accepted it, expecting to return to England after the year. Sleigh went along reluctantly. He was soon teaching a course, significantly titled, “Art and Communication.”

Bennington was a women's college with a strong emphasis on studio practice within its visual and performing arts curriculum, and had established itself as a progressive center for exhibiting and discussing art with staff of the calibre of Tony Smith, Jules Olitski, and Paul Feeley. Its credentials were impressive: in 1952 Clement Greenberg had organized a show of Jackson Pollock's work there, and he followed it with exhibitions by Adolph Gottlieb (1954), Hans Hofmann (1955), and—the show that Alloway saw on his first visit—Newman's first retrospective (1958). Greenberg thought highly of the college and, according to his widow, often remarked “on how much he had gotten out of the tough give-and-take from the Bennington students and faculty.” Greenberg's involvement with the college reached its zenith in September and October 1962 when he ran a weekly series of seminars.