He returned to England, and left again for Barbados in 1639. In Hotten's "Original List of Emigrants" are these records: "Portus Southton, 28 June 1639. Regnald Allen of Kent of 30 yeares gent, Gerrard Haughton of 30 yeares com. Oxon. gen, David Bixe of 35 years com Kanc. gen. free planters of Barbathoes." with five persons named as servants to the planters abovenamed, "they passe in the Boldadventure of hampton for the Isle of Guarnzey from thence they take shipping for the Barbathoes, who have taken the Oaths." His associations with David Bixe continued over the space of many years.
Between 1641 and 1648 several deeds are recorded from which it appears that Capt. Alleyne traded in cotton and tobacco, and actedas agent for Constant Slivester, a London merchant. He also bought and sold land in St. Philip and Christ Church parishes in the neighborhood of Staple Grove plantation, which is mentioned in one of the deeds.
On the 14 July 1643 Reynold Alleyne sold 20 acres of land in Christ Church, Barbados, for 2600 pounds of cotton and tobacco.
On 3 Jan 1642 3 Captain Reynold Allen sold 50 acres in Christ Church to Captain Hilliard for 10,000 pounds of cotton.
In the struggle between the Royalists and Roundheads for supremacy, Reynold Alleyne was and adherent to the Commonwealth. Oldmixon in his 'History of the British West Indies' says: "The system of arbitrary rule which, under King Charles I (crowned 2 Feb 1626, decapitated 30 jan 1648/9) and the system of open opposition to it in arms, which had been carried to such excess in England, did not fail to raise among the colonists similar animosities; but the success of the republicans in Europe gave such advantage to that party in the Barbadoes as occasioned an unqualified opposition to Lord Willoughby, the governor, against whom a deputation of principal inhabitants, requesting assistance, was sent to England in 1650. Amoung these was Colonel Reynold Allen. Their expectation was fully answered; for by a commission for Oliver Cromwell, a considerable military, as well as naval force was sent to them under the command of Sir George Ascough." They reached Barbados on 15 Oct 1651.
For weeks the fleet beat up and down the coast, and it was not until Dec. 7th that early in the morning, under the cover of darkness, a force of between 400 and 500 men, of whom 130 were Scots taken out of the Virginia Fleet, was landed under the command of Col. Alleyne, who having, as Oldmixon says: "a considerable interest in the Island, was supposed to be the fittest man to lead the soldiers to gain it."
They were met by 1200 foot and troop of horse under Col.Gibbes which had been assembled to oppose them. The Commonwealth men made good their footing; the fort was taken and afterwards razed to the ground; four houses burned and four great guns thrown into the sea. Of the landing party, six or eight were killed and thirty wounded, amoung the latter was Col. Alleyne, who received a musket shot when landing. Mrs Alleyne was granted a pass to go on board the Rainbow to visit her husband who succumbed to his wound, being lamented as "a man of worth and honour."
Reynold Alleyne's estate was sequestrated with that of others of the same party by Act of Legislature dated 12 Sept. 1651, towards defraying the cost of the defences by the Royalists, one-fifth only being reserved for the relations of those dispossessed.
He made his will on 16 June 1650 being then a resident of Barbados, but "by Devine
Providence appointed to depart this Island." Mentions: Deare wife Mary Allen one-third part
of all moveable estate, and one-third part of all lands and profits of same during her
natural life, after debts are paid. To sonne Abell, one-third part of all lands and goods
when he is 21 years of age. To sonnes Reynold and Dix and "ye child my wife now goeth with"
one-third part of whole estate. To daughter Mary, out of profits of his estate during his
son's minority and over and above their "Bringing up" 500 pounds Sterling on her marriage
or her age of 18 years. "and the like proportion to ye child my wife now goeth with if a
daughter." Wife Mary Alleyne sole executrix. "I earnestly intreate Collo. Henry Hawley and
Major Valentine Hawley, Lt.Thomas Lukumb and Mr. Thomas Sayer to be assistant unto my said
wife and to be guardians of my children in their minority." Witnesses: Bartine Clarke,
aged about 40 years. Will Howe, aged about 30 years. Proved 14 June 1652.
Source