Stephen Littleton was the eldest son of George Littleton and Margaret Smith, daughter and heiress of Richard Smith of Shirford, Warwickshire. Some sources say that he was a cousin of Humphrey Littleton, but according to the pedigree appearing in Nash's Worcestershire, Stephen and Humphrey were nephew and uncle respectively [1]. They were also related to John Littleton, M.P. of Hagley House, Worcestershire, who had been arrested for his role in the Essex Rebellion and who had died in prison in 1601 [2].

Stephen's principal place of residence was Holbeche House in Staffordshire, which was the scene of a desperate last-ditch effort by the principal conspirators to resist the authorities. He was regarded as being a prominent figure in the catholic community in the Midlands [3]. In the proclamation issued for his arrest on 18 November 1605, he was described as "a very tall man, swarthy of complexion, of browne coloured haire, no beard, or little, about 30 years of age" [4].

Stephen and Humphrey were friends, possibly even cousins, of the brothers Robert and Thomas Wintour. As a result, they were known to other members of the main group of plotters, but they were not considered to be suitable for the principal engineering of the plot. During a visit to Huddington Court at which both Robert Catesby and the Littletons were present, Catesby spoke to the Littletons of the plans to raise a regiment to fight in Flanders, and offered Stephen a command post in this regiment. It is likely that until the events which followed the gathering at Dunchurch and the siege at Holbeche House, this was the extent of Stephen Littleton's knowledge of the plot [3].

With this limited degree of knowledge of what was really being planned, Stephen and Humphrey Littleton joined the Midlands group of conspirators whose aim was organise themselves into a company to reinforce the Flanders regiment. Besides the Littletons, the members of this group included Robert Wintour, John Grant, Henry Morgan and Robert Acton [2].

Stephen and Robert Wintour joined the party which had collected at the Bull Inn in Coventry and which later moved on to the Red Lion at Dunchurch [2][3] Although Humphrey Littleton deserted the party at Dunchurch [2][5], Stephen remained with the group during the flight from Dunchurch to Holbeach House. He was among those who received communion at the hands of Father Hammond alias Hart at Huddington Court on the morning of 7 November [2].

After the party arrived at Holbeach House in Staffordshire, Stephen and Thomas Wintour went to visit Sir John Talbot, who was staying at his estate of Pepperhill which was near Holbeach House. Sir John was the father-in-law of Robert Wintour, a wealthy and prominent Catholic landowner in the region and heir to the earldom of Shrewsbury [6]. The conspirators believed that their cause would be greatly assisted if they could obtain Sir John's support [3][5].

However, Wintour and Littleton were unsuccessful in their attempts to persuade Sir John to join them, and they returned to Holbeche House quite disheartened. On the way back, they were met by a messenger who told them of the accident which had occurred at Holbeche in which some gunpowder which had been placed in front of the fire to dry out had exploded, severely injuring some of those present. Wintour and Littleton understood from the message that the conspirators were dead and that "upon which sight the rest dispersed (i.e had fled Holbeche House)" [7].

After hearing this news, Littleton lost heart and suggested to Wintour that they should both flee for their own safety, but Wintour decided to continue on back to Holbeche alone, while Littleton fled [5] (Other sources indicate that Littleton fled from Holbeche House itself, instead of during his return [3][8]).

Robert Wintour was among those who had also lost heart after the accidental explosion, and he too fled Holbeach House. Wintour and Littleton met up at a point about half a mile from Holbeche House, and from then on they lived the life of fugitives [2][8]. For two months they hid in barns and houses in Staffordshire and Worcestershire, before eventually making their way to Hagley House, home of Muriel Littleton, widow of Stephen's kinsman John Littleton who had participated in the Essex Rebellion [8]. Mrs Littleton was absent in London at the time, but the fugitives were taken in and sheltered by Humphrey Littleton, before being betrayed by one of Humphrey's servants, the cook John Fynwood [1][2][8].

Littleton was tried, condemned and executed for giving assistance to the conspirators and joining them in open rebellion. He was executed at Stafford, together with Henry Morgan [3][4]. Father John Gerard writes that "at his death he acknowledged the fact, and said he did it only for religion, for which he was ready and willing to die. He showed great resolution and devotion, to the satisfaction of all the country.

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