The Pickering family originally came from Westmorland, and acquired Titchmarsh, in eastern Northamptionshire, in 1553. Gilbert Pickering (great-great-grandfather of Sir Gilbert) purchased manors in the village of Titchmarsh, Northamptonshire.

William Earl of Worcester in the 7th year of Edward VI. sold Tichmersh and Aldwincle to Gilbert Pickering (great great grandfather to Sir Gilbert Pickering [1611-1668], and his sons John, James, and Boniface. John Pickering, Est. died in the thirty-third year of Queen Elizabeth. Gilbert descended from an ancient and respectable family in the county of Westmorland. He was the second son of John Pickering of Gretton, second son of Sir James Pickering of Wynunderwater, Knt.

On the north side of the chancel of the church of Tichmersh the principal burial place of the Pickerings, are several monumental inscriptions, including: Sir John Pickering, of Tichmersh, Knt. who died in 1627.