He was the youngest son of the first Simon, was married in 1702 to Sarah Drake, by whom he was the father of Roger, Elizabeth, Alexander (died young) Erastus and Epaphrus (twins, both of whom died young), Erastus, Ursula, Oliver (who later signed the Declaration of Independence), and Mary Ann (or Mariann).
Roger Wolcott was colonial governor of Connecticut in 1751-1754.
Roger Wolcott was a Representative of South Windsor in the Connecticut general assembly in 1709; rose to the bench of justices in 1710; accompanied expedition against Canada in 1711; elected member of council in 1714; Judge of County Court in 1724; Judge of Superior Court, 1732; Deputy Governor and Chief-Justice of Supreme Court, 1741. In expedition against Louisbourg in 1745 he was commissioned Major General by Governor Shirley of Massachusetts and was second in command to Pepperell. He arrived at Cape Breton with the troops 30 April and 17 June the city of Louisbourg capitulated and the provincial forces entered it. Governor of Connecticut, 1750-54.
In addition to his political activities he published three pieces or works. The first was poetical, his second publication was ecclesiastical and his third political. He also wrote an account of the Pequot War in verse.
The Rev. Samuel Wolcott in the Memorial says: "We have no portrait of him. In one of the political squibs of the day he is referred to as 'Stately, smoking Roger.' For the following description of his public appearance, in his official costume, we are indebted, through a friend (Hon. Isaac W. Stuart), to a lady in Wethersfield, Miss Marsh, the daughter of a venerable clergyman long since deceased, who gives it as she received it from her mother, who had often seen him in her childhood: 'He was a visitor at her father's, and the costume of an officer under the regal government was too imposing to pass unnoticed. Several times a week he rode out on horseback, and never appeared abroad but in full-dress. He wore a suit of scarlet broadcloth. The coat was made long, with wide skirts, and trimmed down the whole length in front with gilt buttons, and broad gilt vellum button-holes, two or three inches in length. The cuffs were large and deep, reaching nearly to the elbows, and were ornamented, like the sides of the coat, as were also the pocket-lids, with gilt vellum buttonholes and buttons. The waistcoat had skirts, and was richly embroidered. Ruffles at the bosom and over the hands were of lace. He had a flowing wig, and a three-cornered hat with a cockade; and rode slowly and stately a large black horse, whose tail swept the ground.'
"A little north of his residence in South Windsor was a public road to the river, where he owned a ferry, connecting with Plymouth Meadow on the other side, the right of which was granted him by the General Court, in 1725. His house was about a third of a mile north of the present meetinghouse. He built it in 1704, the year of the attack on Deerfield, and the walls of the front room were covered with a painting descriptive of that scene. The house was taken down a few years since, and some of the panels, which belonged to that apartment, are preserved in the neighborhood as relics. He spent the last years of his life with his daughters. Mrs. Newberry, in Old Windsor, and was buried there with his fathers, although his home had been on the other side of the river. His estate was inventoried at (pound sign) 1,805, 4s, 2d., and was distributed among his surviving sons and daughters, and the children of his deceased son Roger."
An obituary appeared in the Connecticut Courant of 27 July succeeding entitles "Memoirs of the Life and Character of the Honorable Roger Wolcott, Esq., late Governor of Connecticut" (portions are omitted).
"This great and good man was descended from honorable parents. He was one of those happy few whose minds seem to be formed with an original strength and force, not to be suppressed by misfortune or want of exterior advantages; and though this did not appear early, yet, like the hidden gem in the mountain, was daily ripening, in due time to be produced to light, polished, and make a shining appearance in many exalted stations in life.
"As soon as he left his master, he was determined to have a liberal education, if possible, but on taking an inventory of his estate, he found it not to amount to fifty pounds, so he was obliged to drop that design; but, still unalterably determined not to remain in a state of ignorance, he borrowed such books as he could get, and read with attention; and, having a retentive memory and solid natural judgment, what he read he retained, digested, and made his own. He got an acquaintance with men of the best abilities of his time, and by an indefatigable industry and application got acquainted with most branches of literature; for he was an exact chronologer, well acquainted with history, ecclesiastical and civil, and geography both ancient and modern, and with the Newtonian Philosophy, and most of the curious discoveries of the moderns.
"He had a taste for the Belles Lettres; and some poetical pieces he has left behind, to show that, had his Genius been well cultivated, he might have made a considerable figure among the Sons of the Muses.
"But the law and arts of government were his favorite study. Accordingly, he soon made his appearance at the barr, where he distinguished himself so far as to be soon called into public employment.
"He filled the post of Governor, as he had the rest, to good acceptance, till the affair of the Spanish ship, a considerable part of whose rich cargo being embezzled through the indolence, inadequateness, and inattention of the Spanish merchant, the freemen were by some designing person made to believe that the loss was occasioned through Governor Wolcott's fault, and that the people must be taxed for repayment.
"He retired with composed, unruffled grandeur, cheerfully referring it to Divine Providence to find means to evidence that innocence that he had an inward consciousness of; nor were his expectations disappointed, for we suppose every one is now fully convinced that that affair was well conducted, -- and that to a wonder, considering its suddenness, and the little acquaintance this Colony had in affairs of this nature.
"After his retirement from public life, he divided his time between devotion, reading (which was principally church history, and the works of the most celebrated divines, especially Doct. Owen and Doct. Bates), agriculture, -- his beloved employ, --and the enjoyment of his friends.
"And though his constitution was excellent, yet as he knew that, in the course of nature, the time of his departure was at hand, his great and constant business was to stand with his loyns girt and his lamp burning, waiting for the coming of his Lord. Thus he lived till about the middle of April last, when he complained of a disorder in his legs, which soon turned of a livid color, his strength from that time declining fast, till Sunday, May 17th, on which day, about noon, his constitution (firm as it was), not being able to longer support itself, sunk under the weight of old age, he being then in the eighty-ninth year of his age.
"His funeral was, agreeable to his own directions, attended without much pomp or show; at which time the Hon. Deputy Governor Trumbull, and Hezekiah Huntington, Esq., from the Upper House, and eight of the principal members from the Lower House being specially appointed for that purpose by the General Assembly, then sitting in Hartford, attended, and delivered a message to the mourners, wherein they did honor to the wisdom, patriotic spirit, religion, and virtue that adorned his life, and expressed their full approbation of his public services in the various posts he sustained in this Colony.
"His body was strong and well proportioned, his countenance and deportment particularly adapted to command reverence and esteem; his wit was ready, and uncommonly bright; his method of reasoning (free from sophistry) was clear, nervous, and manly, as became a generous inquirer after truth, and not a noisy wrangler for victory only. He was a sincere, unfailing friend to every industrious, virtuous, honest man, who acted his part well, whatever was his station in life; but the indolent sluggard, and soft enervated, unexerting debauchee was his aversion. All persons of true piety were his delight. He was a true friend to regular and firm government, and was an equal enemy to tyranny on the one hand, and licentiousness on the other. He thought that the practice of industry, economy, frugality, and temperance was the only way to relieve this Colony, and America in general, from their present distresses and therefore was often recommending them.
"He was a wise legislator and an able statesman. While he was a judge, he held the balance of justice with a steady unwavering hand; and being far superior to venality, or the influence of personal, family, or party connections, he pronounced the law impartially, on all the cases brought before him. As a governor he appeared to advantage; this was his proper element, for he seemed originally formed to govern. He was a kind and provident husband and parent. His moral character was unblemished, his religion and piety were unaffected; and he died as he had long lived, a member of the Second Church in Windsor. In short, we take this to be one of the few lives spent in so useful and exemplary a manner, that 'tis worth while to hold it up in view of the world, as being in general worthy of their imitation."