The Pickering family originally came from Westmorland, and acquired Titchmarsh, in eastern Northamptonshire, in 1553.
Pickering won Northamptonshire’s second seat in 1626, with the approval of both Spencer and the sheriff, Sir Richard Knightley*, defeating Sir Lewis Watson* of Rockingham in a heated contest. He at first assumed that he could also rely on Montagu’s support, but the latter in fact championed Watson, causing great anxiety to Pickering in the run up to the hustings; nevertheless, a strong base of support in the town of Northampton ensured him the victory.
On 19 Jan. 1627 Pickering appeared before the Privy Council with several of his Northamptonshire neighbours for refusing the pay the Forced Loan, and ten days later was committed to the Gatehouse.
