At nine o'clock in the morning late in the autumn around the year 1556 or 1557, Richard Sheale, minstrel, harper and mediocre poet, rode out alone from his home town of Tamworth on the border of Shropshire and Staffordshire and headed south. He carried with him, or so he subsequently claimed, roughly sixty pounds in gold, with which he intended to clear his debts in London. Sheale's wife was a ‘sylke woman’, that is, a kind of peddler, and sold shirts, skirts, smocks, neckerchiefs, ribbons, edging, silk thread and linen at fairs and markets in the vicinity of Tamworth. Sheale too may well have supplemented his income as a minstrel by selling merchandise of this kind. His friends in London had provided him with both cash and merchandise on credit, allowing his wife to carry on her business, and now, at the end of the peddling season, he was on his way down to London to clear the debt, having changed his money into gold to make it the easier to carry.

No doubt Sheale hoped that along the way he would have an opportunity to play his harp to alleviate his poverty. Some of the songs he knew were old ones, like the famous ballad The Hunting of the Cheviot which told how the reckless Harry Percy led a raid into the borderlands and met and killed the redoubtable Lord Douglas, only to be captured himself.