The oldest monuments in Preston Bissett may be two ring-ditches seen on aerial photographs west of Tingewick airfield. These may be the ploughed out remains of Bronze Age barrows, mounds that covered burials, but nothing else is known about them.
Preston Bissett is recorded in Domesday and was part of Bernwood Forest in the medieval period. Bernwood had been a hunting forest from the time of Edward the Confessor. It grew to its largest extent under Henry II. The whole area was not covered by woods; in the medieval period a forest was a place where deer roamed for hunting and so included open land, villages and fields. All those who lived in the forest were not allowed to hunt or even gather wood without a special licence from the king. Bernwood Forest was finally disafforested in the reign of James I in 1635, although it had been shrinking in size since the time of King John (1199-1216).
There are the remains of a moat, a fishpond, some house platforms and hollow-ways near Cowley Lower Farm. Medieval documents record the site of a chapel here, in Parson’s Close, and there was obviously a small settlement called Cowley that was later deserted. The farmhouse dates to the 17th century. There is ridge-and-furrow around Preston Bissett that is the remains of medieval farming, preserved when the land was turned to pasture.
Threebridge Mill is recorded from the 13th century and maybe from Domesday. A windmill mound is known close to Cowley Old House and is recorded as ‘le windmill hill’ in a 17th century document. Small scale excavation recovered some medieval pottery. 13th century pottery was also found at Thorpe’s Farm, suggesting that this 18th century house had a medieval predecessor. The moat next to the White Hart may also point to a medieval predecessor to this 17th century former pub.
The oldest surviving building in Preston Bissett is St John the Baptist’s church, which was built in the 14th century, though some 12th century masonry reused in the building suggests there was a church here before this one. It was also much altered in the 15th century. Other listed buildings date back to the 16th century, such as 1 & 2 Beech Cottage; the 17th, such as The Old Hat pub; and the 18th century, such as Bittersweet Cottage. Some 19th century privies from an unknown location in Preston Bissett were donated to the Chiltern Open Air Museum and can be seen there reconstructed – though not for use!
One of the later changes was the construction of the Great Central Railway, which was opened in 1899. Though now closed, cuttings and structures can still be seen along its length.