It appears that Herberfeld began his career in the employ of Hugh Benet† of Oxford since a William Herberfeld was listed among Benet’s servants in 1394.
In all probability, Herberfeld held at least some of his property at Oxford in the right of Cecily, whose interests also extended well beyond the town. Probably the maternal grand-daughter of William Audley, Cecily was recognized to have a claim to several former Audley manors in and around Fareham and Hambledon in Hampshire. In 1418, she and Kingsmill had made a formal release of the manors to Thomas, Lord Camoys, and other trustees, apparently acting on behalf of the heirs of Reynold Curteys. Seven years later, she and Herberfeld quitclaimed the properties to several of the same trustees, who in return undertook to pay the couple an annuity of 20 marks during her lifetime.
At the time of his marriage to Cecily, Herberfeld had already begun his career as a municipal office-holder. He served two consecutive terms as a bailiff in 1417-19, during which time he was involved in a quarrel between the town and Osney abbey, the largest landowner in Oxford. The quarrel, which had broken out in 1415, resurrected old grievances. At the end of Edward III’s reign, the abbey had won an earlier dispute over the right to exercise jurisdiction in the villages of North and South Osney. By the early fifteenth century, however, the abbot was complaining about the town’s continued attempts to usurp that right and, by 1417, the quarrel had descended into violence. A servant of the abbot stabbed a tax collector from the town and John North, one of Herberfeld’s immediate predecessors as bailiff, claimed that the abbot and a couple of his fellow canons had led an assault against him. For his part, the abbot complained that over the past decade and more a number of prominent townsmen had systematically encroached upon his land at Osney. He also alleged that the mayor, Walter Dauntsey, and bailiffs, Herberfeld and John atte Wode, and other leading burgesses had broken into his weirs at North and South Osney, plundered his fishery, taken away his goods and horses and assaulted and imprisoned his tenants and servants. At the end of 1418, the Crown appointed a commission of oyer and terminer to investigate the complaints submitted to it by the abbot and John North, leading to a resolution of the dispute by arbitration 11 months later. Bailiff again in 1426-7, Herberfeld became one of the aldermen of Oxford in 1428.
Soon after attaining the latter office, Herberfeld and his fellow townsmen were embroiled in a dispute between their corporation and the chancellor of the university, who had challenged the corporation’s right to levy market dues on sellers of victuals in the town. In the autumn of 1429, the mayor and other municipal officers, including Herberfeld, received a summons to the university’s convocation, where they duly appeared and denied imposing illegal exactions on the victuallers. During the quarrel, both sides appealed to higher authority, and it was in pursuit of such support that Herberfeld and William Brampton* went to London in late 1429 or 1430. During their time in the City, they were allowed a supper costing 12d. at the corporation’s expense.
Having attested the election of Oxford’s MPs to the Parliament of 1437, Herberfeld appears to have retired from public affairs. In his will, dated 18 Nov. 1438, he requested burial before the altar of the Holy Cross in the parish church of St. Martin. He bequeathed sums of money to St. Martin’s and other religious institutions in Oxford or elsewhere in Oxfordshire, requested that a chaplain should sing for his soul for a period of three years after his death and set aside no less than £20 for those bridges and roads in and around Oxford most in need of repair. He also directed that every chaplain attending his funeral should receive 6d., asked his wife to reward each of his servants at her discretion and instructed his executors to distribute ten marks among Oxford’s poor within a year of his death. Herberfeld provided for his son Thomas and Thomas’s wife Margaret by settling the couple’s place of residence, a messuage in the parish of St. Mary Magdalene, upon them for their lives in survivorship, with reversion to Thomas’s children. Presumably, Thomas also succeeded to those parts of his father’s real estate not mentioned in the will. Herberfeld provided for his own wife by assigning another messuage in the same parish to her to hold for the rest of her life, after which it was to be sold for the good of his and her souls. Finally, Herberfeld left the residue of his personal estate to Cecily to dispose of for the benefit of his soul. He appointed two executors, Cecily and his fellow townsman and draper Roger Fullys, and asked William Begenill, the rector of St. Martin’s and a doctor of both laws at Oxford university, as their overseer. Following his death, the will was registered with both the prerogative court of Canterbury and the municipal authorities at Oxford. The Church’s copy bears no date of probate but that entered in the town’s ‘Liber Albus’ records that it was proved before the mayor of Oxford on 27 May 1440.