There is a great deal of prehistoric activity in Pitstone parish. The quarries in the parish have been useful for uncovering this. A Neolithic to Bronze Age crouched burial with a flint knife and an undated (but possibly prehistoric) ditch was recorded in Pitstone quarry 2 and an Early Iron Age hearth, post-holes, storage pits associated with pottery and animal remains from Pitstone quarry. Neolithic flint has been recovered at Duncombe Farm in a field-walking survey; a Neolithic flint axe in the garden on Glebe Close; a Neolithic polished stone axe near the railway; Palaeolithic to Early Bronze Age flint flakes, blades and cores, a fragment of Neolithic stone axe and arrowhead were found in the Marsworth Road allotments; Neolithic flint flakes, blades, scrapers and cores were found on Moneybury Hill; a Palaeolithic flake, Neolithic to Bronze Age scrapers, flakes and blades were found in field-walking north of Brook’s Statnalls Wood; and a Neolithic blade and a Middle Bronze Age urn fragment were found in a rabbit hole on Pitstone Hill and Neolithic flint flakes close to a possible Neolithic flint mine, also on Pitstone Hill.
Other prehistoric monuments are known from aerial photography. An Iron Age subcircular enclosure is known at Church End and Neolithic to Bronze Age ring-ditches are known at Cowhill Spring and close to the church. A late prehistoric boundary at Incombe Hole was also sampled in trial trenching. Some upstanding monuments include a Neolithic to Bronze Age barrow on Moneybury Hill, parts of an Iron Age cross-dyke on Pitstone Hill along with possible Iron Age settlement remains, though these may be later in date. Settlement dating to the Late Bronze Age to Early Iron Age; Roman; Saxon and medieval was recently excavated at the former cement works on Vicarage Road.
Roman and medieval pottery and other artefacts were found in a field-walking survey near Duncombe Farm; Roman tile was found in digging a land drain at Pitstone Green Farm; and Roman pottery was found at Church Farm. A Late Iron Age to Roman enclosure with a possible Late Iron Age kiln and pits and Roman ditches, cobbling and well with associated animal bone and pottery was found in excavation in Pitstone quarry. Possible Roman or medieval field systems and hollow-ways were recorded on the Ashridge Estate. A possible Roman temple was partially dug in the 1930s though it has since been damaged by metal-detectorists.
There are quite a few Saxon remains known from Pitstone. Yardley Farm may be the site of a medieval or Saxon moot, a mound used for meetings. Saxon burials have also been found in Pitstone rag-pit and quarries. In fact, quarry 2 seems to have been the site of a sixth to eighth century cemetery. Tenth century pottery was found near Church Farm and eleventh century settlement features and medieval pottery was found in excavation on Pitstone Hill.
Medieval features include five pillow mounds, often used as rabbit warrens, were recorded in field survey on Pitstone Hill. Some medieval settlement features and artefacts were also seen south of the church and a moat is known at Yardley Farm. A medieval bone knife handle, tile and pottery were found in the cement works and a medieval enclosure was recorded at Sallow Copse. Several manors are known from historical documents, Pitstone manor itself, Morrant’s manor, Yardley manor and Barley End manor. There are also historical records of a dovecote at Barley End in the sixteenth century. There are also records of a chalk-cut horse on Pitstone Hill that probably dated to the post-medieval period.
Brook End is suggested by local tradition to have been the site of a medieval or post-medieval courthouse. St Mary’s church is the oldest surviving building and dates to the thirteenth century with some fourteenth and fifteenth century additions. White Friars is the oldest secular building, dating to the fifteenth and sixteenth centuries. The other listed buildings in the parish are sixteenth or seventeenth century and timber-framed, such as Orchard Farm or Greenacres.
There are historical records of a mill from the thirteenth to eighteenth centuries and a fourteenth century predecessor of the more recent windmill. There were several mills in Pitstone. There are nineteenth century records of the surviving millhouse, bakehouse and outbuildings. It is a seventeenth to eighteenth century cornmill known from eighteenth century maps. Another postmill is known from nineteenth century maps but it was destroyed in quarrying. Beesley’s Mill is a nineteenth to twentieth century watermill. Pitstone Windmill is actually in Ivinghoe parish.
There are a few twentieth century monuments that deserve mention. There was a cement works established in the 1930s in Pitstone, it closed in the 1990s. The building is now a set of offices and is listed. A bomb crater was recorded on an aerial photograph near Down Farm and the landowner confirmed its interpretation.