The Old Hall, or ‘Watling Street’ as it was often known from the fifteenth century, was the stem seat of the Forester family – now represented by Lord Forester of Willey Park (q.v.). The Forester family was certainly resident in the Wellington area, as keeper of the fee of Wellington Hay, from the twelfth century. A Hugh Forester was mentioned in 1187–1197 and then a successor, Robert Forester (fl. circa 1200–27) held half a virgate in chief by the service – or serjeanty – of keeping the King’s hay. This became a hereditary office that descended in the family. By the early sixteenth century, John Forester (d. circa 1521) took a lease of the Wellington Hay Estate, which passed to his son, John Forester the younger (fl. 1544 and d. 1591), who was described as ‘of the Watling Street’, the name then given to the house. He was a Freeman of the Company of Pattenmakers and of the court of Henry VIII, from which he was granted the right, in 1520, to wear his bonnet in the presence of his monarch owing to a head injury. That unusual right has passed through the Forester family and is still referred to by current family members as its ‘hat trick’. This younger John might have been the member of the family who was able to acquire the freehold of the property in 1555.

John Forester was married to Joyce, the daughter and heiress of Philip Upton, of Upton Magna and Oteley, and his wife, Anna Steventon of Dothill. Their youngest son, William, was the father of Francis Forester (1571–1637).

Francis married Cicely, the daughter of Andrew Charlton of Apley (q.v.) and is thought to have been the builder of the east wing at the Old Hall as well as building the house at Arleston, an adjoining property. Arleston is said to have been built as a hunting lodge, in anticipation of a visit from James I, and remains a handsome house with two timbered wings of differing length, the longer one dated 1614 and the shorter dated 1630.