Just before 1500, the Littleton family make their first appearance in Penkridge. Richard Littleton brought Pillaton into the family's possession through marriage and Pillaton Hall was the Littleton family seat for about 250 years, the centre of an expanding property empire. Soon they took on the leases of most of St. Michael's church lands and established a family chapel in the church – a statement of their growing importance. They were the most important local representatives of the landed gentry, a class that was to dominate rural life for several centuries.