By the beginning of Elizabeth’s reign Winchelsea had ceased to be of any maritime importance, for the sea had receded. The government of the town, nominally in the hands of the corporation, was increasingly influenced during this period by the neighbouring gentry families. This shift of power was reflected in the parliamentary elections, when Winchelsea returned local gentlemen rather than townsmen and merchants. These were held by the mayor, jurats and common assembly. At the time of the elections for the 1559 Parliament, the wardenship of the Cinque Ports was vacant. The mayor, Goddard White, and his deputy, John Pecke, were elected, but for some reason Henry Fane I, a Kent gentleman, was substituted for the latter. It seems likely that Pecke stood down in favour of Fane, whose family had a little property in Winchelsea. Had this happened at a later election, it could have been attributed to the influence of the 10th Lord Cobham, a close friend of Fane. Cobham was not yet lord warden, but it may be that he was already sufficiently influential to secure Fane’s return. In 1563 Fane was reelected, together with an unidentified Member, Richard Chambers, who may have been a Sussex gentleman. It is not known why Chambers did not take his place in the 1566 session. In all probability, he died. He was replaced by Henry Brooke alias Cobham I, the lord warden’s brother.

In 1571 Winchelsea readily allowed the lord warden to choose one Member, Robert Eyre II. The other MP, Wilford, was a jurat of the town who lived at Heding over the border in Kent. Wilford was re-elected in 1572, when he was mayor, and was joined by Richard Barrey, the lord warden’s deputy and lieutenant of Dover castle.

Before the 1584 election, the lord warden wrote to the Ports that he had received letters from the Privy Council, requiring him to ensure that a good choice was made of burgesses in the Ports. Winchelsea thereupon decided to by-pass the lord warden and wrote direct to the Privy Council, explaining that the town in the past ‘was not in so good state as presently it is to serve in the parliament’. This letter was accompanied by a list of ‘six or eight of the most meet persons for that purpose’, the Council to ‘like or mislike at their pleasure’, together with a messenger to answer any questions. At a subsequent assembly on 3 Nov., Dr. Giles Fletcher was elected ‘in accomplishment of the letters of ... the Privy Council’, together with Herbert Pelham, a local Sussex gentleman, who had recently become a jurat of Winchelsea. This was too much for the then lord warden, who appears not to have intervened again in elections at Winchelsea. Five local gentlemen were returned in the next three Parliaments: Adam Moyle, Thomas Egleston and Ashburnham Pecke, all town officials; Herbert Morley, the son of a former mayor; and Adam Ashburnham, one of a family with longstanding connexions with Winchelsea.

In 1597 Henry Brooke alias Cobham II*, 11th Lord Cobham, succeeded his father as lord warden, and wrote to a number of the Cinque Ports asking for nominations. At a meeting of the assembly held on 7 Oct., Winchelsea ‘agreed to gratify his honour’, and Cobham chose Ralph Ewens, a servant of (Sir) John Stanhope, while at a subsequent meeting of the assembly, 15 Oct., Thomas Colepeper of Wigsell was chosen as the town’s nominee on condition he took a ‘corporal oath’ to maintain the town’s privileges ‘as a baron should do’. Cobham again nominated in 1601 and this time chose Hugh Beeston, a friend of his brother-in-law, (Sir) Robert Cecil, while the town chose a Kent country gentleman, (Sir) Moyle Finch of Eastwell.

Winchelsea rarely paid anything to its Members. In 1586 it promised 20s. to Adam Moyle ‘towards his charges’.2