A short section of Grim's Ditch delineates the northern end of the village, which lies within the civil parish of Cholesbury-cum-St Leonards.

The earliest evidence of habitation is indicated by a short section of the Chiltern Grim's Ditch linear earthwork, which is believed to have been constructed during the Iron Age.

A charter of Henry de Crokesley from around 1187 refers to him granting the manor at Dundridge to Missenden Abbey and setting aside land for the chapel-of-ease at St Leonards.

[3] The choice of Leonardus or Leonard may have been in recognition of a hermit associated with Missenden Abbey known as the 'Hermit of the Woods', according to the Pipe Rolls of 1196.

Blakemere is thought to be a reference to Black Mere, a marshy area and pond that appears in records from that time.

Despite the Dissolution of the Monasteries the church continued in use as a chapel-of-ease until after 1586 when an inquisition was held in the name of Queen Elizabeth into why the chapel and lands had not reverted to the crown.

However following successful pleas from Silvester and Henry Baldwin, it was permitted that from 1587 services could be held there once again, for the benefit of local woodsmen, because Aston Clinton church was a good hour's walk away, and the long journey stopped them from getting on with their work).

The building was largely rebuilt in a simple Queen Anne style around 1700, paid for by the brother of John Wood, the then minister.

Dundridge Manor house is recorded to have fallen into disrepair at the time it was disposed of to the Darvill (Darell) family.

Though Sylvester did not survive the journey, the Baldwin family successfully settled in the newly established New Haven Colony on land adjacent to the present day Milford, Connecticut, from where it spread out across the continent.

Bacheler's close association with court life is evidenced by a contemporary mural of Sidney's funeral procession to St Paul's Cathedral in 1587, which depicts him astride a horse.

He is credited with introducing consort music and was a contemporary of John Dowland who was a lutinist at the Court of James I, whilst Bacheler had been elevated to Groom of the Privy Chamber, a position of significant trust as confidant to Anne of Denmark.

Having ceased trading in 2015, an attempt to change use to residential was unsuccessful; and so through until June 2021, the pub premises were being refurbished under new ownership.