Berry acquired a reversion as Porter (gaoler) at Ludlow Castle in 1572, but he held office only briefly in 1596-7, and probably came to Ludlow after his appointment as surveyor of Crown estates in Herefordshire and Shropshire in 1575. It was in this capacity, in 1601, that he claimed he had earned the Crown nearly £1,300 in fines as a common informer. He also held a reversion as clerk receiver of fines at Ludlow, although this was taken away in 1602 at the insistence of lord president Zouche.
Berry owed his municipal status to his readiness to act as solicitor for the town’s frequent lawsuits at Westminster, the assizes and before the Board of Greencloth, as often as once or twice a year, in addition to his regular service at Parliament.
In 1604 Berry was returned to the Commons for an eighth time, together with bailiff Richard Benson. The most important task the two men were charged with was to procure a new charter, a project mooted at various times over the previous year. The earlier charter of 1596 had been the focal point of the disputes between the oligarchy and their rivals, and the new grant was presumably intended to smooth over past differences. Berry and Benson secured the charter at a cost of £66 9s. 1d.,
The general election of 1614 saw strong pressure at Ludlow to elect outsiders, presumably from lord president [Ralph] Eure†: Berry and recorder Sir Robert Townshend, a justice at the Council, were chosen, but Berry was quickly reported to the Commons for returning himself, being then high bailiff. He conceded this point under examination, and, as precedents for the removal of mayors were deemed to apply in his case, his return was rejected on 14 April.
