In 1625 Pickering graduated with a BA from Emmanuel College, Cambridge and in 1629 entered Gray's Inn. Gilbert Pickering was an MP representing Northamptonshire and as such served in the Short Parliament of 1640 and in the Long Parliament of 1640 to 1653. He abandoned the royalist cause when Charles raised his standard at Nottingham in 1642. In 1642 Pickering joined the Northamptonshire committee and was most active as "a sequester and a committee man" although he also raised a regiment for parliament. As the decade went on he moved towards becoming a Presbyterian, by stages until he was an Anabaptist,. During the disagreement between Parliament and the New Model Army in 1648 Pickering sided with the Army and kept his seat in the Rump after Pride's Purge of the Long Parliament. He was appointed one of the judges at the trial of Charles I in 1648 but only sat in two sessions and did not sign Charles's death warrant. He remained MP for Northamptonshire through the Interregnum 1648–1660 and was appointed Lord Chamberlain to Oliver Cromwell in 1657. His public career ended in 1660. With the help of his brother-in-law Edward Montagu, 1st Earl of Sandwich, Pickering obtained a pardon from King Charles II. The original of the pardon delivered by Charles II on vellum in Latin is in the Pitts Theology Library of Emory University, MS no 109.
Family
Pickering's family came to prominence at the time when Sir Gilbert's great-great-grandfather Gilbert Pickering purchased manors in the village of Titchmarsh, Northamptonshire. Pickering's father, John Pickering, married Susannah, daughter of Sir Erasmus Dryden. Sir Gilbert married Elizabeth, daughter of Sir Sidney Montagu, master of requests and a prominent Parliamentarian and his first wife Paulina Pepys, great-aunt of Samuel Pepys. They had eight sons and four daughters. Sir Gilbert's baronetcy was created in about 1632, his son John inherited the title, and his son Gilbert inherited it from him. Edward, the fourth to hold the title, died without issue 3 July 1749, at which time the title became extinct. Gilbert had a brother called John who also fought for Parliament dying in 1645, which means that there were three generations of John Pickering in the same family related to Gilbert thus: father, brother and a son who inherited the baronetcy. Pickering was also the cousin and an early patron of the poet, John Dryden. John Dryden grew up in the village of Titchmarsh. The monuments to the poet Dryden and to his parents Erasmus Dryden and Mary Pickering were erected at Titchmarsh by Elizabeth Creed, whose marriage at Titchmarsh in 1668 was attended by Samuel Pepys, who was a cousin of Lady Pickering. Sir Gilbert and his descendants are commemorated by tombs and memorials in Titchmarsh church.
