Hawkenbury was settled before Tunbridge Wells itself was founded in the 17th century, and at one time fell within the parish of Frant, lying as it then did in Sussex. It was originally known as "Hockenbury".

Bacon's 1912 map of Tunbridge Wells shows the centre of Hawkenbury lying along Hawkenbury Road, being that area currently lying south of the recreation ground. The Victorian estate around Sibby's Corner was not then considered part of Hawkenbury. Hawkenbury had no less than four places of worship, being a Congregationalist chapel (now United Reformed Church) at Sibby's Corner, a St. Peter's Mission on the junction of Forest Road and Napier Road, an unnamed church on Hawkenbury Road (below the present site of Hawkenbury Mews) and a second Congregationalist chapel lay below the present site of the Hawkenbury Road allotments, as did a number of village dwellings. Beyond agriculture, the residents were employed in the Brickfields, lying due east of present-day Maryland Road. South of Brickfields were a plethora of now-vanished farm buildings, the remains of which can still be traced from the footpath off Chieveley Drive. In 1912 Halls Hole Road was called Marlpits Lane and Whybourne Gate Farm lay on the site of the current Whybourne Cres