Born in Yeovil, Somerset, to Irish parents, Cregan joined The Falcons, When aged fourteen, which was formed whilst he attended Poole Grammar School. After developing his next band "The Disastisfied Blues Band", Cregan briefly joined with future Traffic frontman Dave Mason, in "Julian Covay and the Machine" in 1967 and moved on to join the rock and soul band "The Ingoes" as a vocalist and guitarist. This band soon morphed into the psychedelic Blossom Toes the same year, who later turned to guitar-led rock.