Joseph Dale was brought up within a respectable working class family in Chorlton Row, then on the outskirts of Manchester. He attended church every Sunday with his parents and his brothers and at Sunday School he learnt to read and write and, when old enough, he was always in employment and showed no sign of becoming involved in criminal activities. As he got older, however, he began to rebel against his strict upbringing. He stopped going to church, left home and began to frequent Manchester's many public houses, where he learnt to play cards and to gamble. One result of his erring ways was that he began to find it difficult to keep in employment. It was during a period of unemployment that Dale met two petty criminals, Charles Taylor and John Bratt, at the Two Greyhounds public house in the centre of Manchester.
Bratt told Dale and Taylor that he could get the three of them employment with a relative of his in Castleton, North Derbyshire. With this promise in mind, on July 16th 1823, the three men set out on the long walk from Manchester to Castleton. It is likely they were aware that to get to Castleton, they would have to pass through Chapel-en-le-Frith, where the annual Wakes Week was taking place. As they would not have had much money between them, Bratt and Taylor were most likely prepared to indulge in some petty thieving to pay their way. Thus, when they came across William Wood, a seemingly wealthy traveller, at the Bulls Head public house near Stockport, the opportunity to rob him was too good to miss.
Following their attack on Wood, the three men went on the run, spending the same night in Buxton and then the next morning walking to Macclesfield, where they bought themselves new suits of clothes. They then returned to Manchester, heading straight back to the Two Greyhounds. Incredibly they seemed completely unaware that sporting such fine new clothes would raise suspicions of how they came about them.