Beginning in the years of the Norman Conquest until roughly Tudor times, the Scudamore/Scudemore surname was mainly associated with a few aristocratic families in Herefordshire, and also in Gloucestershire, and Wiltshire, and Hertfordshire. American genealogist Warren Skidmore has stated in his extensive research on the surname: "Up until Tudor times, Skydmore was Skydmore's cousin everywhere." Ralph de Scudemer was a stonemason, brought over from Normandy by the English King Edward the Confessor before the Norman Conquest, around 1060, to help to build castles along the Welsh border, as the Saxons knew little of stone castle-building and were building castles mainly of wood. Meanwhile, the Normans were already masters of stonemasonry techniques. The first of these castles which Ralph helped to construct was at Ewyas Harold, Herefordshire. Although the castle no longer stands – it had fallen into disrepair by the 16th or 17th century, and most of the stone from it was carried off and "recycled" to build or rebuild certain houses in the village – its motte and keep, perched on a low hill overlooking the village, the River Wye, and the gently sloping Herefordshire countryside, can still be plainly seen a millennium later. Ralph made quite a name for himself as a stonemason in Britain, as he is mentioned five times in the Domesday Book of 1086, often as an undertenant at the castles which he helped to build: Opeton in Wiltshire; Fifhide ; an unnamed parcel of land at Ewyas Harold, which Warren Skidmore postulates was probably Kaureos, now Corras in Kentchurch; Poscetune ; and Little Hatfield. These lands can be traced over the next few generations – in some cases, dozens of generations – as they were passed down to the families and descendants of his three sons, Reginald, Walter, and Hugh. Scudamore descendants still occupy Kentchurch Court at Kentchurch, Herefordshire. This 'immigrant generation' is also the last generation in which the family's lands were known to have been equally divided among Ralph's three sons; by the next generation, the English laws of primogeniture had largely taken over. By the mid-12th century, the descendants of Ralph de Scudemer – with elder son Reginald's successors taking over the family's caput at Upton Scudamore in Wiltshire, while Walter's descendants remained in Herefordshire – were listed as witnesses to charters bearing the clearly Norman surnames "d'Escudamor" and "Escudamore." These names would morph into the Scudamore surname over the next generation or two, and then later into "Skydemore" and "Skydmore" by 1400. The name "Skidmore," sometimes also spelled "Skydmore," is a variant of the earlier, but still extant surname "Scudamore." As late as the 17th century, and possibly later, it is documented that some people of this surname used both names interchangeably. For example, a family might be known as "Skidmore" during the week, but be called "Scudamore" when attending church services on Sunday. The patriarch of the Birmingham family mentioned below, for example, William Skidmore, was most often recorded as "Skidmore" in church registers and tax lists, but spelled his name "Skudemore" in his will.
By the sixteenth century, around the time that parish registers began to come into common use following the Reformation, the shorter variant "Skidmore" came to be more common, and began to spring up in other areas of the United Kingdom where it had not previously been documented in the aristocratic or landowning families. It was also around this time that it ceased to be the case that "Skydmore was Skydmore's cousin everywhere," i.e. it could no longer be said with certainty that all people using this surname were definitively descended from Ralph de Scudemer. "New" Skidmore/Scudamore families such as the large, proliferant ones in the western suburbs of Birmingham and "the Chalfonts" – Chalfont St Giles and Chalfont St Peter in Buckinghamshire – could not be proven by traditional genealogical means to have been related to the earlier families in Herefordshire. By the 1600s, Skidmore families began to pop up in the American colonies, and later in Australia, as well as many other places around the world. More details on these branches can be found in Warren Skidmore's book "Thirty Generations of the Skidmore/Scudamore Family in England and America."