Chilton parish is home to a variety of historical sites, including an Iron Age settlement located east of Chilton Grove. This site was uncovered during the construction of two pipelines, the Southern Feeder and a parallel pipeline from Aylesbury to Chalgrove. Archaeologists discovered a pit and several ditches, which suggest that the site may have been the edge of a settlement. Artifacts found at the site date back to the Mesolithic to Early Bronze Age, including a flint blade found along the Southern Feeder pipeline, and a Mesolithic blade discovered in allotments on Brill Road.
While there is little evidence of Roman activity in the parish, a few pieces of Roman pottery have been found during excavation work, such as in ditch-digging south of Wombwell Farm, in a stream north-west of Westfield Farm, and during the construction of the school.
Chilton and Easington (Hesintone) were both recorded in the Domesday Book and were separate manors that belonged to Bernwood Forest. The forest was originally a hunting ground established during the reign of Edward the Confessor and grew to its largest extent under Henry II. In the medieval period, a forest was a place where deer roamed for hunting, and so included open land, villages, and fields. Those who lived in the forest were not allowed to hunt or gather wood without a special license from the king. Bernwood Forest was disafforested in the reign of James I in 1635, although it had been shrinking in size since the time of King John (1199-1216).
Easington was a larger settlement in the medieval period, and earthworks from the time can be seen in aerial photographs around the present hamlet. Local tradition suggests that Easington had a chapel in the medieval period, and a 19th-century map records a field named Millway near Lower (Easington) Farm, in which there was a mound that could have supported a windmill. However, it has since been levelled, and only a piece of millstone was found nearby.
In Chilton, a medieval moat was discovered from aerial photographs located southeast of Hornage Farm. St. Mary’s church is the oldest standing building in Chilton, built or rebuilt in the 13th century and restored in 1907. Several secular buildings in Chilton also date back to the medieval period, such as Wheelwrights, a timber-framed hall-house with 16th century additions located southwest of the church. Others date to the 17th and 18th centuries, like Hornage Farm, White Cottage, and The Thatch.
John Croke, the lord of the manor in the early 16th century, designed his own gardens around 1529, which later became part of Chilton Park. A hunting lodge was built in the 16th century (c. 1544) when Chilton Park was enclosed as a deer park. This lodge was later altered in the 18th century and is now known as Chilton Park Farm. A map of Chilton House grounds from the 18th century records a pond, which can still be seen southeast of the house and may have been used for breeding fish or ducks. While Chilton House itself is from the 16th century, it was enlarged and altered in about 1740. There are records of a dovecote and malt-house at the house from the 17th and 18th centuries.
Lastly, there is field-name evidence of a brickworks at Chilton Grounds Farm in the post-medieval period, and there are records of extraction pits in the playing fields and south of the old vicarage in the 19th and early 20th century.