He was apprenticed to a butcher, but when he was caught stealing livestock, he joined a notorious gang of deer-stealers and smugglers in Essex. This gang also made a practice of robbing farmhouses and terrorizing the women in the absence of their husbands and brothers, and Turpin took the lead in this class of outrage. Upon the breakup of the gang, Turpin went into partnership with Tom King, a well-known highwayman. To avoid arrest he finally left Essex for Lincolnshire and Yorkshire, where he set up under an assumed name as a horse dealer.
Harrison Ainsworth , in his romance Rookwood, gives a spirited account of a wonderful ride by Dick Turpin on his mare, Black Bess, from London to York, and it is in this connection that Turpin's name has been generally remembered. But as far as Turpin is concerned the incident is pure fiction. A somewhat similar story was told about a certain John Nevison, known as "Nicks," a well-known highwayman in the time of Charles II, who to establish an alibi rode from Gad's Hill (near Rochester, Kent) to York (some 190 miles) in about 15 hours. Both stories are possibly only different versions of an old north road myth.