In his day and generation Benjamin Skiffe was the most prominent man in Chilmark and held a commanding posi-tion in civil and military affairs throughout the county. Indeed, he was the leading citizen of the Vineyard, after the death of Matthew Mayhew. Benjamin was next to the youngest of the four sons of James Skiffe, Senior, who came to the Vineyard. He was born Nov. 5, 1655, probably in Sandwich, where his father resided and had been a prominent citizen for many years. He was a witness to a deed in Tisbury on Dec. 4, 1677, [*Dukes Deeds, I, 267.] and it is probable that he had gone to Tisbury before that with one of his brothers, either James or Nathaniel, as an inmate of their homes. [*James came to Tisbury in 1671 and Nathaniel before 1674. The younger brother Nathan does not appear on record till 1675.] There he first saw the young girl who had lately moved there from Hampton, and who first attracted his admiration.
The girl, Hannah, daughter of Joseph Merry, was five years his junior, and on Feb. 20, 1679-80 they were married. Where they set up housekeeping is not known, but the next record we find of him is a purchase of land in this town on Feb. 6, 1681, consisting of a tract on the west side of Roaring brook. [*Dukes Deeds, I, 233] The next year on July so, 1682, he bought the land called "Nathaniel's Neck," but it cannot be determined whether either of these were used by him as a place of residence. [*Ibid., I, 346] From all evidences he still remained in Tisbury and is called of that town in 168I, 1682 and 1688, and on March 17, 1687, was chosen town clerk there. [*Tisbury Records, 18.] He was elected county commissioner in 1686, apparently to represent Chilmark, as the other two were citizens of the sister townships. He continued to act as town clerk of Tisbury from his first election in 1687 to 1693 inclusive, and not until 1695 is he called "of Chil-mark." He was a proprietor of one share in the town, how-ever, in 1692. [*Court Records, Vol. I. It is difficult to separate the relations of proprietors and residents, as there were non-resident proprietors who were entitled to hold office and draw lots.] His residence was on the east side of the Fulling Mill brook, not far from the site of the mill which stood on its banks, in sight of the South road. He bought one hundred acres on Feb. 13, 1694, jointly with Pain Mayhew, and it is supposed that it was for the purpose of carrying on the mill which he had erected there for fulling cloth. [*Dukes Deeds, I, 233.] Two years later he bought the mill privileges of New Mill river "to improve for a mill," but it is not known whether another one was built there by him. [*Ibid., I, 125.]
When the great political change of jurisdiction over the Vineyard took place in 1791, it appears that Skiffe was one of those who did not like the transfer, and he took sides with the Mayhews in the policy of passive opposition. "Capt'n ben Skiffe," wrote Simon Athearn in October of that year, "have bene very bussie against the government from this place," and as a consequence he recommended that Skiffe be super-seded as Captain of the military company as "the most likely way to bring the company to obedience." [*Mass. Archives, CXII, 424.]
But Athearn was not able to carry his point in this matter, and Skiffe continued to be a leader in military affairs as well as in civil life. He was for some time prior to 1792 Captain of the Foot Company of Militia of Tisbury and Chilmark combined, and is referred to as Captain Skiffe in 1693 and 1695. In 1703 he appears as Major Skiffe and thereafter is known by that title, and late as 1709 he was in command of this body of troopers. [*Savage says he was employed "in an important trust" by Governor Dudley in 1704, but the author has no data in confirmation of it (Gen. Dict., IV, 706).]
The town availed itself little of his services in an official capacity. For three years only, 1706-7-8, he served it as selectman, but his time was in requisition for more important duties to which the whole island unanimously called him. In those days the three towns, as at present, sent but one repre-sentative to the General Court, and for five years, 1707-1711, 1715, and 171 7, he was the "member from the Vineyard." [*Chilmark Town Records, 6, 7, 8; Tisbury Records, 62.] In 1716 Edgartown voted to send him again if Chilmark would join, but it does not appear that this was done. [*Edgartown Records, II, 79.] In 1700 he was one of the judges of the Court of Common Pleas for this county, and on the death of Matthew Mayhew in 1710, Major Skiffe was Appointed Judge of Probate for this county in suc-cession arid held the office until his own decease eight years later. It will thus be seen that this man was one of the fore-most men of his time, whom all were ready to honor with such marks of confidence and respect as was in their power to bestow. He seemed to have stood well with the influential Mayhews and thus steered clear of the difficulties into which his brother fell by antagonizing them. There is an entry in the town records of Edgartown significant of the esteem in which he was held by other communities. On Jan. 22, 1707-8, the town voted that "Major Benjamin Skiffe, Esqr. shall be requested by their Clerk, Thomas Trapp, to be at their next meeting at Edgertown to assist them in their public or common affairs as moderator; and do order their said clerk to request the same in their behalf." [*Ibid., II, 90.] This appears to be an unusual and unique compliment.
Major Skiffe, in his last illness, made his will on Feb. 15, 1717-18, and died two days later. He left a large property which was inventoried by the appraisers on Feb. 23, 1719, and returned as amounting to £2748-10-5, probably being the richest man in the town. [*Dukes Probate, I, 65-7.] He was childless, but had adopted young Beriah Tilton (23), born in 1703, and to him he bequeathed, subject to Mrs. Skiffe's contingent interest, the homestead and mill adjoining. He also gave bequests in his will to his niece, Sarah Athearn, daughter of his brother Nathan, and to his brother-in-law, Thomas Pease. The following is an abstract of his will:
To Hannah my dear and loving wife … my sole executrix … all my estate … to dispose of as she sees fit if she dont dispose of the same in her life time then my will farther is that Beriah Tilton, a lad that now dwells with me, shall have my housing, mill and lands adjoining. … to Sarah, wife of Solomon Athearn of Tisbury, a certain tract of land lying in the Town of Chilmark, near the Stone Wall pond, being partly purchased of the Indians & not purchased the lands intended being held by me under Col. Thomas Dongan. I give her the whale of said tract as well the right to purchase as the already purchased.
I give to my brother Nathan Skiffe the right of purchase or patent right in a certain tract of land lying at Monamesha in the town of Chil-mark, which patent or right of purchase I had of Major Matthew Mayhew, deceased.
I give to Thomas Pease of Edgartown all the right title and interest which I have to any lands in Sanchacantucket Neck. [*Dukes Probate, I, 63.]
His widow survived him many years and died Feb. 27, 1758, at the great age of 98 years. They lie buried in the Chilmark burying ground on Abel's hill. She was a woman who partook of the distinctions accorded to her honored husband, and was called and known as Madame Skiffe. At her death she bequeathed to Beriah Tilton her "whole and sole personal estate" and made him executor. She had dis-posed of her real estate by deeds of gift and otherwise, but the homestead and mill remained in his possession as designed by her husband. [*Ibid., IV, 53.] This property descended to Beriah's son William and thence to his children, and was held by descendants till about 1897, when it was sold to George W. Blackwell.
Source: The History of Martha's Vineyard by Dr. Charles Banks: Volume II, Annals of Chilmark: pp. 29 - 41