At Maddle Farm much research has been done into the nature of Roman farming practices. There was once a simple villa there with a large agricultural estate based on long narrow fields of the Roman type: 47 hectares of arable land with an additional 850 hectares of pasture. It is estimated that this could have supported between forty and eighty people (including a workforce of about thirty). They apparently lived in the associated Roman village at Knighton Bushes.

Upper Lambourn had its own manor, owned by the De Bathe family in the 13th century. Henry de Bathe was notorious for being a corrupt judge. He is known to have taken many bribes and, in land dispute, often passed judgment in his own favour. He resided quite often at Up-Lambourn Manor and, in 1240, gained permission, from the Dean of St. Paul's, to built a private chapel there. This survived until the reign of Queen Elizabeth I, when it is recorded as being in ruins. From the De Bathes, the manor was inherited by the De Bohun Earls of Hereford. Not surprisingly, they were rarely seen there. By the 1600s, it was in the hands of the Essex family from Lambourn proper.

Near the junction of two tracks, just north of the hamlet, sits one of Berkshire's three 'Hangman's Stones'. It probably marks the site of an old crossroad gibbet, but an old legend says otherwise. Apparently a young sheep-stealer sat down here for a rest whilst carrying his ill-gotten gains on his shoulders, feet tied with a rope across his throat. While he slept his grip loosened, the sheep struggled and the sword of justice fell!