Pilgrimage of Grace began on October 13, 1536, after the failure of the Lincolnshire uprising earlier that month.
Robert Aske, barrister, led the uprising, which soon gathered a following of up to 40,000. Aske presented the peoples’ desires for an end to the suppression of the monasteries and other religious changes, referencing the protection of the Church promised in the Magna Carta! His pilgrim band/army far outnumbered Thomas Howard’s forces, but he wanted to negotiate a solution. Through Norfolk, Henry promised to convene a Parliament in York to address the issues if the rebels disbanded and returned to their homes. Aske also met with Henry in London. When another uprising broke the truce, Aske was arrested and tried.
David Knowles pays eloquent tribute to him in Bare Ruined Choirs: The Dissolution of the English Monasteries:
". . . he showed himself the most loyal and able contemporary champion and apologist of the Tudor religious, and his death cannot be allowed to pass without a memorial of words. He is indeed one of the few men of his age whom we recognize at once to have been utterly frank and single-minded . . ."
As Knowles continues, he describes how much Aske contributed to the progress of the Pilgrimage of Grace and yet demonstrates how aspects of Aske’s character led to its failure:
"Robert Aske, not Henry, was the true representative of all that was most characteristic and most sincere in England. [Yet] he failed because, when the call to build his tower had come suddenly upon him, he had not fully reckoned the cost."
Aske was not prepared to defy his king, to treat with Henry VIII as Henry VIII would treat with him, with force and deceit, and he was not prepared to defeat his king, to take him down if necessary:
"The leader of a rising should have been prepared, if need arose, to put his cause before his king; else it were better to have remained silent and hidden."
Aske thought he could trust his king to respond to the concerns of his people and to fulfill his promises. He did not want to use the force his army of pilgrims represented, and so, he failed.
Knowles concludes however:
"Of all leaders of revolts that have failed, Aske is one of the noblest. He was deceived and killed by the king whom he would gladly have served and whom he loved and trusted ‘not wisely but too well’."*
As Knowles’ memorial to Robert Aske makes clear, he was the better man in his dealings with Henry VIII because he was honorable and honest. Knowles further comments that only force could have stopped Henry VIII—but how far could that force go? If Aske had been willing to transform that group of pilgrims into an army, pitch battle against Thomas Howard, defeat him, then what? March to London and raise a siege on one of Henry VIII’s castles? Take the castle, capture Henry, and then execute him? Ultimately, this story demonstrates the limits even of military force.
Only Henry could have put the needs of his people above the needs of his power and responded to the Pilgrimage of Grace and Robert Aske as they deserved. In his mind, however, they deserved only punishment. He exacted brutal reprisals against the leaders of the uprising. Aske endured, not just the usual punishment of traitors, to be hung, drawn, and quartered, but the even more agonizing death of being hung from the battlements at York Castle, left to die of exposure and dehydration.
Henry VIII’s third wife, Jane Seymour, tried to speak up in defense of Aske, the Pilgrimage, and the monasteries, but Henry warned her that speaking up and interfering with his will had brought about the fall of her predecessor. Jane heeded his warning and was silent.
*David Knowles, Bare Ruined Choirs: The Dissolution of the English Monasteries. Cambridge: The University of Cambridge Press, 1967, pages 219-220. Another book I'd recommend is by Geoffrey Moorhouse: The Pilgrimage of Grace: The Rebellion that Shook Henry VIII's Throne.