Woolley was born in Weymouth, Dorset and attended Allhallows College, then in Honiton, for about 18 months, but then moved with his parents to the Union of South Africa upon their retirement.
Woolley returned to the United Kingdom and studied for a further MA degree in Mathematics and, later, a PhD at Gonville and Caius College, Cambridge.
[9] Woolley is known for his initial disbelief in the practicalities of space flight, a notion he shared with Sir Harold Spencer Jones, his predecessor as Astronomer Royal.
Terry and John Rudge pointed out that the quotation ascribed to Woolley is actually a misquotation of what he actually said (as they had heard themselves on Radio Newsreel).
Terry and Rudge report that Woolley's statement was: "All this talk about space travel is utter bilge, really."
"Anyone", said Terry and Rudge, "who had seen the flamboyant articles about space travel and the imminent colonisation of the moon and planets that were splashed all over the newspapers in 1956, with science fiction-style illustrations, must have been immediately aware of what the new Astronomer Royal was riled about.