In the medieval period there were two boroughs facing each other across the narrow entrance to the estuary of the river Wey: Melcombe Regis (in the parish of Radipole) on the north bank, and Weymouth (in that of Wyke Regis) on the south. That their histories remained separate and distinct stemmed initially from the grant of the port of Weymouth by Henry I to St. Swithin’s priory, Winchester. It was to St. Swithin’s too, that, in 1248, a market and fair were granted to be held at Weymouth, and it was the prior who in 1252 conceded to the inhabitants their first charter. This stated that the port was a free port, and that the town was a free borough entitled to enjoy immunities and privileges similar to those of Southampton. The priory then sold the estate of Weymouth, Portland and Wyke to the bishop of Winchester, who in 1259, however, exchanged it for lands in Oxfordshire until then held by Gilbert de Clare, earl of Gloucester. Weymouth continued for a time to be part of the Clare estates, eventually brought by Elizabeth de Burgh in marriage to her husband Lionel, duke of Clarence, and through his daughter, Philippa, to the earls of March. During the period under review the town was held for a short while (1398-c.1405) by Eleanor, widow of Roger Mortimer, the 4th earl of March, and then passed into the custody of the Crown until 1413 when the 5th earl, Edmund, came of age. From his death, in 1425, until 1432, during the minority of the next heir, Richard, duke of York, it was in the hands of Humphrey, duke of Gloucester. Thus, unlike Melcombe Regis, which had been a royal borough since the 13th century, Weymouth was not accountable to the Crown until 1461, when its lord, Richard of York’s heir, Edward, became King.2

As the profits of the borough were paid to the officers of the lord of the estate (in this period to the earl of March’s receiver at Cranborne) and not into the royal Exchequer, and as few of the estate papers of the earls of March have survived, it is not clear whether or not the town prospered in the late 14th century. Earlier on Weymouth had contained about 260 burgages and was larger than Lyme Regis. Nevertheless, it was small in comparison with most of the Channel ports, not even having a church of its own. Although Weymouth and Melcombe may then have been similar in size, the lay subsidy returns of 1323 point to a disparity of wealth, since in Weymouth 32 burgesses were taxed a total of £6 1s.6d., but in Melcombe 30 were taxed at £9 0s.6d. Weymouth, however, appears to have got the better of disputes between the two ports. In 1332 local jurors asserted that the water between the towns belonged entirely to the southern borough; and although in 1367 it was declared that the boundary between them in fact lay in mid-stream, the burgesses of Weymouth were at that time successfully diverting vessels from Melcombe to their own quay, to the profit of themselves and their lord. Melcombe may have temporarily benefited from the establishment of a Staple in 1364,3 but subsequent depopulation and growing impoverishment were to cause it in 1433 to be displaced as a head port by Poole and reduced to the status of a creek. Weymouth probably fared better. For one thing, the southern borough was easier to defend and suffered to a lesser extent from French attacks. The sums paid by the burgesses of Weymouth into their lord’s coffers varied from year to year: they amounted in 1303 to £13 8s.8d., in 1314 to £14 8s.8d., in 1399 to £14, in 1422 to £20 1s.9d. and between 1447 and 1478 to £16 19s. a year on average. It might be inferred from these isolated figures that the period under review was a comparatively prosperous one for the town, yet in 1435-6 Weymouth appeared on the list of Dorset boroughs stated by royal commissioners to be depopulated and desolate, and the burgesses were allowed a remittance of £2 on the payments due for parliamentary tenths. In the 16th century Weymouth was numbered among the decayed towns of the shire in need of restoration.4

Weymouth was not represented in Parliament at all in the reign of Edward I, and it was only rarely that it returned Members before that of Richard II. Regarding the period under review, the returns for the Parliaments of 1390 (Nov.), 1401, 1404, 1411, 1413 (Feb.), 1415 and 1416 are all now missing, and such as have survived reveal little about the electoral procedure. It seems likely, however, that parliamentary elections were held in the town and were merely reported at the shire court. After 1406 it became customary for Weymouth (like the other Dorset boroughs) to send four delegates to Dorchester to inform the sheriff of the town’s choice. The names of the delegates, together with those of the elected representatives from all the boroughs of the shire, were returned to Chancery on one indenture. The names are known of 31 men who sat for Weymouth in 23 of the 32 Parliaments convened between 1386 and 1421, inclusive. As many as 20, two-thirds of the total, sat in the Commons only once, so far as is recorded. And, in fact, only two Members were in any way outstanding as regards service of this kind: John Bassingbourne, who was returned six times between 1385 and 1421, and Robert Penne, who sat in seven Parliaments between 1402 and 1421 (on one of these occasions, however, doing so for Melcombe). In no less than 15 Parliaments, one of the two representatives, and in four more (1391, 1414 (Nov.), 1420 and 1421 (May)) both had been returned before. By contrast, perhaps in as many as eight Parliaments both Members were newcomers to the Commons, but the gaps in the returns make it impossible to say whether this was, in fact, the case. Re-election in the strict sense occurred seven times: John Bassingbourne was re-elected in 1395 and 1410; John Wodham in 1414 (Nov.); Robert Hillary in 1420 and Robert Penne in 1419, 1420 and 1421 (May). The last named, who thus sat in four successive Parliaments, was replaced in each of the next two (1421 (Dec.) and 1422) by a kinsman, John Penne. Other Weymouth families, such as those of Fleet, Brice and Payn, also established something of a tradition of parliamentary service. At some point in their careers three of the Weymouth representatives sat for Melcombe: Robert Penne in 1404 (Jan.), William Clerk I in 1406, and John Brice II in 1425. Robert Hillary, who was returned twice for Weymouth, was later, in 1427 and 1433, to appear in the Lower House for Bridport and, in the meantime, in 1429, for Dorchester.

As many as 26 of the 31 known parliamentary burgesses for Weymouth evidently resided in the town. Nothing is recorded about four of the rest, but their obscurity in itself strongly suggests that they were local men. In fact, only one of the Members, Robert Hillary, was definitely an outsider. Seven of the resident burgesses held property elsewhere, on the nearby Isle of Portland (John Bassingbourne and John Penne), in Dorchester (William Ford, John Penne, John Wydeford and Stephen Russell), or in Bridport (Philip Brice). Russell laid the foundations for his family’s later prominence in the shire by marriage, while Thomas Cole I came into lands outside Dorset, in Somerset, by inheritance from a distant relative. Except for Russell and Hillary (who was described as a ‘gentleman’), none of the representatives for Weymouth in this period could be classed as landed gentry. On the other hand, the occupations of only a third of their number have been discovered. As might be expected, these ten were engaged in commerce, importing wine from Gascony and exporting cloth, ropes and grain. The most outstanding among this group was Russell, whose alias ‘Gascoigne’ indicates where his main trading interests lay. Without doubt the parliamentary representation of Weymouth in this period was dominated by its merchants. Only one of the MPs, Hillary, is known to have been a lawyer. By sitting in the Commons twice, towards the end of the period (1419 and 1420), he anticipated a later trend in the borough’s representation.

The charter of 1252 had permitted the burgesses to choose their own bailiffs, provided that these officials did fealty to the lord of the manor, or his steward, at the next court held after Michaelmas following their appointment, at which time the outgoing pair were to account for the issues of the borough. It is not now possible to compile a complete list of the bailiffs of our period, but even so 15 of the MPs are known to have served a term in this office. In the case of 12 of them this preceded election to Parliament. There are only two known instances when parliamentary service and municipal office coincided: in September 1397, when William Ford, one of the burgesses then up at Westminster for Richard II’s last Parliament, was elected bailiff; and in December 1421 when William Payn was returned during his second bailiffship. Three of the Members for Weymouth are known to have occupied minor posts in the employment of the earls of March, either as ‘messor’ of the manor of Wyke Regis (Philip Brice and John Penne) or as bailiff of the liberty of Portland, Wyke and Weymouth (Brice and John Bassingbourne). Although Brice was ‘messor’ at the time of his return to Parliament in 1391, there are no signs that the Mortimers ever attempted to influence elections at Weymouth, or to place other of their friends or servants in the borough’s seats.

Very few of the MPs for Weymouth ever held offices in the Crown’s appointment. Four acted as collectors of customs at Melcombe (John Bassingbourne (1395-8), John Wydeford (1411-12), William Payn (1416-17) and Robert Penne (1417-19)), the last named, Penne, being appointed during his third Parliament for Weymouth and still employed when returned to his fourth. Philip Brice, who was controller of the customs in 1390-2, was elected for the second time in 1391, also while in office. John Bassingbourne served for three years (1396-9) as alnager in the shire at large, for much of this time also occupying the post of customer at Melcombe. Only five of the representatives were appointed to royal commissions of a more casual sort, of which most were concerned with local affairs. William Ford was twice named as a collector of parliamentary subsidies in the whole shire, however, and Robert Penne acted on a commission of inquiry active in Somerset as well as Dorset. The lawyer, Robert Hillary, served quite often as a commissioner in both shires, occasionally even as one of the quorum. Not only was he appointed to deliver Dorchester gaol, but was also a member of the Dorset bench. Nevertheless, his first appointment as j.p. was not to take place until 12 years after his last return for Weymouth. Hillary was the only one of the Members to establish social connexions of any real note: he was for some time associated with Bishop Stafford of Bath and Wells. But although this particular attachment possibly influenced his acceptance as parliamentary burgess by the towns of Bridport and Dorchester later on in his career, it can hardly have affected his elections for this borough.