John Pickering was born in 1615 at Titchmarsh in Northamptonshire, the son of a family of Puritan gentry. His brother Gilbert later rose to become Lord Chancellor to Oliver Cromwell. John trained as a lawyer, and later served Parliament on diplomatic duties in Scotland and England, before and during the Civil war.
He assisted, as a civilian, when the Earl of Manchester took control of the Eastern Association, a grouping of counties under Parliamentarian control. In early 1644, John took command of a regiment of dragoons, and in March, saw his first action at the storming of Hillesden house in Buckinghamshire. His dragoon regiment comprised men of poor quality, and was disbanded soon after.
In March 1644, he took command of a newly formed Eastern Association infantry regiment, which became known as “Colonel John Pickering’s Regiment of Foote”, recruited in Suffolk, Essex and possibly Norfolk. Their colours (flags) had blue as their background colour. There is no record of their coat colour, but it is likely to have been red, with the cuffs of their sleeves turned back to show a blue lining.
The regiment was prominent in the storming of Lincoln in May and the siege of York in June. On July the second 1644, Pickering’s distinguished themselves at the battle of Marston Moor. They then helped to clear the Royalists garrisons from South Wingfield Manor, Belvoir Castle, Sheffield House, Bolsover Castle and Staveley House. With the rest of Manchester`s Army, they joined the London brigades and the Earl of Essex`s Army at the second battle of Newbury. During the abortive attack on Shaw House, they advanced singing psalms, for like many Eastern Association units they, or at least their officers, were ardent Independents or Puritans.
By January 1645, as a result of casualties, sickness and desertion, Pickering’s had been reduced to only 243 men. To fill its ranks Ayloffe`s Regiment, the Aylesbury garrison, was disbanded and its men transferred to Pickering’s. In April 1645, it became one of the original twelve foote regiments of the New Model Army. The regiment saw action at the failed attempt to storm Faringdan House, and then marched to the siege of Oxford. Pickering’s stood at the centre of the front line at the battle of Naseby on the 14th June 1645. The regiment had been brought up to strength with many raw conscripts, and it was not surprising that, together with most of the front line, they were seen to “flee like men possessed”, their officers and colours falling in with the reserve. The regiment was rallied, in time to take part in the Armies complete victory over the king`s army. There after they marched with the new model to recapture Leicester, and then into Somerset to defeat the Royalist Army of the South west at Langport on the 8th of July, then onto the storming of Bridgewater on the 23rd of July, Sherborne Castle on the 10th of August and Bristol on the 10th September.
With Cromwell, they took Devizes, Laycock House, Winchester, and October 14th stormed Basing House. They then joined the siege of Corfe Castle and finally the siege of Exeter. Whilst at Army headquarters at Ottery St. Mary, near Exeter Colonel John Pickering, like many of his soldiers, caught the new disease, probably Influenza. He died on the 24th November 1645 and was buried in December at Lyme Regis. The regiment he commanded had become a respected hard fighting unit, often at the forefront in difficult and dangerous actions. It was taken over by his second in command and as Colonel John Hewson`s Regiment of Foote continued its proud record.