On August 20, 1962, Bob Dylan signed a contract which made Grossman his manager. Grossman also extended hospitality to Dylan at his home in Woodstock in upstate New York. Dylan liked the area so much he purchased a house there in 1965. The cover of Dylan's album "Bringing It All Back Home" was photographed at Grossman's home in Woodstock. The woman in the cover photo with Dylan, in the red trouser suit, was Grossman's wife, Sally. Having returned to Woodstock at the end of his 1966 World Tour, Dylan was on his way home from Grossman's house in West Saugerties when he suffered the motorcycle accident that precipitated his eight-year withdrawal from touring.