The Loyalists of Massachusetts and the Other Side of the American Revolution

by James Henry Stark

He stood upon the uppermost heights of society, he reached every elevation that could be obtained, and there was nothing left for ambition to covet, because all had been gained. He was the first native-born general and the first native-born governor. The governor acquired the highest military rank and had engaged in active and successful warfare with the highest command in New England. He presided over the legislative, executive and judicial departments of the government. In addition to his military and civil distinction he acquired that of being the most delightful companion in the colony. He lived on his ample paternal domain and his hospitality was magnificent and the attractions of the festive board at Careswell were heightened by the charm of his beautiful wife. He was elected governor in 1673, which office he held until his death. He was succeeded by his only surviving son.

Isaac Winslow, born in 1670 and died Dec. 6, 1738. This eminently distinguished man sustained the chief places of power and honor in the colony, and was a worthy successor to his father in being its chief military commander, a member of the Council for more than 20 years and for some time its president, and for several years Chief Justice of the Court of Common Pleas, and Judge of Probate; the last office he held at his death. His eldest son, Josiah, graduated at Harvard College in 1721, was killed in battle with the French and Indians at Georges Island, May 1st, 1724. His second son, great grandson of the first governor of Plymouth, was the celebrated

John Winslow, born in Marshfield, May 27, 1702, and died in Hingham, 1774, in his 73rd year. No native of New England, probably, except Sir William Pepperell, was more distinguished as a military leader. In 1740-1 he was a captain in the unfortunate expedition to Cartagena under the command of Admiral Vernon, and subsequently endured much hard service in the several enterprises against Crown Point and Nova Scotia. He will be remembered in our annals principally in removing the Arcadians from Nova Scotia. The forces employed by the Colony at this period was composed almost entirely of Massachusetts troops, specially enlisted for the service to act as a distinct body. They formed into a regiment of two battalions, of which Governor Shirley was the Colonel, and of which Winslow, then a half-pay Captain in the British army and a Major-General in the Militia, was Lieutenant-Colonel. As Shirley could not leave his government to take command in person, Monckton, a Lieutenant-Colonel in the Army, was appointed to conduct the first battalion and Winslow the second. The plan for abducting the Arcadians was kept a profound secret, both by those who formed it and by those who were sent to execute, the home government knew nothing about it and it appears to have been done solely by the Colonial government; Colonel Winslow was but the instrument and acted under the Governor's written and positive instructions.

In 1756 Major-General Winslow took the field with eight thousand men raised in New England and New York to repel the French invasion and marched against Montcalm, who to save Crown Point and Ticonderoga made a movement from Oswego by the St. Lawrence River. As soon as the French General returned to Canada, Winslow and his army returned to Massachusetts.

In 1762 he was appointed with William Brattle and James Otis to act as Commissioner "to repair to the river St. Croix, determine where the easterly line of Maine is to begin and extend the said line as far as should be thought necessary." In compliment to General Winslow, "the fourth of a family more eminent for their talents, learning and honors than any other in New England," one of the towns on the Kennebec River in 1771 was called by his name. Of this town he was one of the original grantees. He died at Hingham in 1774, aged seventy-one, leaving two sons and a widow, who embarked with the Royal Army from Boston in 1776. She was in England in 1783, and enjoyed a pension from the government.

Pelham Winslow, eldest son of General John, was born June 8th, 1737, graduated at Harvard College in 1753, and entered the office of James Otis to fit himself for the bar, was a staunch loyalist. In 1774 he abandoned his home to escape mob violence and took refuge in Boston. At the evacuation in 1776 he accompanied the Royal Army to Halifax, and thence went to New York, where he entered the military service of the Crown, and was Major. In 1778 he was proscribed and banished. He died at Brooklyn, New York, in 1783, leaving a wife and an infant daughter.

Dr. Isaac Winslow, second son of General John, born April 7, 1739, graduated at Harvard College in 1762, died in 1819. He commenced the practice of physic, and though of the same principles as other members of his family, remained upon his estate during the war, and his life, thereby saving it from confiscation, for although he was a strong loyalist his medical services were of such great value to the revolutionists that they did not drive him forth and deprive him of his property. Sabine says: I find it said, and the authority good, that in 1778 he treated about three hundred patients inoculated with smallpox, and such was his remarkable success not one of them died. His son John, an eminent lawyer, deceased at Natchez in 1820. His widow, Frances, died at Hingham in 1846, aged eighty-four. The family tomb of the Winslows is at Marshfield, on the Careswell estate, of which Governor Winslow was the first owner. It was afterwards purchased by Daniel Webster, on which he resided until his death.

Edward Winslow, only brother of General John, born June 7, 1714, died at Halifax in 1784, aged seventy-two years. He graduated at Harvard College in 1765, resided at Plymouth, was Clerk of the Courts, Register of Probate, Collector of the Port. He was obliged to seek shelter in Boston from mob violence, at the evacuation in 1776 went with the Army to Halifax, Nova Scotia, where he died. The ceremonies at his funeral were of a style to confer the highest honors to himself, and his illustrious family. His estates in Massachusetts were confiscated, but every branch of his family was amply provided for by the generosity of the British Government.

Edward Winslow, Jr., only son of the aforesaid Edward. He was born in 1745, died at Fredericton, N. B., 1815, aged seventy years, graduated at Harvard College in 1765. In 1774, the Plymouth County Convention "Resolved, That Edward Winslow, Jr., one of the two clerks of the Court of General Sessions of the Peace and Court of Common Pleas for this County, has, by refusing this body a copy of an Address made at the last term in this County, to Thomas Hutchinson, Esq., betrayed the trust reposed in him, by refusing his attendance when requested, treated the body of this county with insult and contempt, and by that means rendered himself unworthy to serve the county in said office."

In 1775 he joined the Royal Army at Boston, and entering the service became a Colonel. In 1778 he was proscribed and banished. In 1782 he was Muster-Master-General of the Loyalist forces employed under the Crown. After the war he settled in New Brunswick, and was a member of the first Council formed in that Colony, Surrogate-General, Judge of the Supreme Court, and finally Administrator of the Government. The Royal Arms which for many years were displayed in the Council Chamber in the Old State House in Boston, still exist, and are carefully preserved in Trinity church, St. John, N. B. The story of their exit from Boston, and by what means they came to find a permanent home at St. John, were not known till recently, when documents were found, which leave no question or room for doubt.