The Isle of Wight, with an economy dominated by pastoral agriculture, was traditionally and administratively a part of Hampshire, although it possessed a somewhat distinct community with a clearly-defined group of gentry families, many of whom inclined towards royalism in the 1640s. This probably helps explain why Charles I sought sanctuary there on his escape from parliamentarian captivity. The island held its own sessions of the peace with its own justices, and operated its own house of correction. Furthermore, it was exempted from certain local rates and taxes, and possessed a distinct military structure, with militia regiments controlled by a centrally-appointed governor, who was generally able to wield at least some electoral influence on the island.
The island traditionally had three electoral boroughs – Newport, Newtown and Yarmouth. Under the terms of the Instrument of Government, however, the island was granted county status, and empowered to return two knights of the shire, although this effectively replaced the borough of Newport, the island’s capital, since the latter was disenfranchised during the protectorate of Oliver Cromwell*. Although the number of electors is unknown, the island’s adult population was probably between 6,000 and 7,600.
In 1654 Sydenham himself took the second place behind John Lisle*, a native of the island, whose seat lay at Wootton.
Sydenham’s influence was yet more apparent in the election of 1656, when he was returned alongside his deputy, Bowreman, and when he was once more able to nominate his successor when he opted to sit as knight of the shire for Dorset (2 Oct.).
When English constituencies were restored to traditional patterns in 1659, the Isle of Wight ceased to be enfranchised as a county, and Newport was restored as a two-Member constituency, returning Thomas Bowreman alongside Robert Dillington*, grandson of Sir Robert Dillington.
