The first information we have on the Willoughbys is that of Deputy-Governor Francis Willoughby, who had a son Nehemiah, born 18 June 1644, who had a son John, born 11 December 1688. Our John Willoughby might have been a son of the Willoughbys above, but that has not been proven.

In 1745, John and Anna Willoughby moved to Hollis, NH, and two years later, they established their home there on the west side of Pine Hill. He was a grantee of Plymouth, NH, and one of the exploring party who, before the Charter, visited Plymouth in 1762.

John and his wife Anna (Chamberlain) Willoughby had twelve children:

• John, Jr., b. at Billerica, MA 24 Dec. 1735; m. Azubah Wheeler.
• Jonas, b. at Billerica, MA 31 March 1737; d. 1791; m. 10 July 1760 Hannah Bates; residence Hollis, NH.
• Joseph, b. at Billerica, MA 17 Feb. 1739; residence Bennington, VT.
• Anna, b. at Billerica, MA 30 May 1741; m. 3 May 1771 Timothy French; residence Hollis, NH.
• Mary, b. at Billerica, MA 26 Feb. 1743; d. 1752.
• Susannah, b. at Billerica, MA 26 May 1744; d. Sept. 1828; m. 28 Nov. 1764 Jonathan Powers; residence Dunstable.
• Samuel, b. at Billerica, MA 13 Feb. 1745; d. 26 Oct. 1832; m. (1) 3 Dec. 1772 Elizabeth Jaquith; m. (2) Mary Gould.
• Mehitable, b. at Hollis, NH 3 Aug. 1747; m. 19 Oct. 1769 Jonathan Bates.
• Rebecca, b. at Hollis, NH 13 Feb. 1749; m. 1770 Thomas Nevins, Jr.; residence Hebron, NH.
• William, b. at Hollis, NH 2 Sept. 1751; d. Nov. 1773.
• Elizabeth, b. at Hollis, NH 3 April 1753; m. 27 Aug. 1794 Samuel Lovejoy.
• Josiah, b. at Hollis, NH 30 July 1755; d. 1757.

John Willoughby, Jr. was ten years old when the family moved to Hollis, NH. He served three enlistments in the French and Indian War, in Capt. Peter Power's company, Col. Joseph Blanchard's regiment, from 24 April to 25 November 1755; in Capt. Amos Gage's company, Maj. Thomas Tash's battalion from 21 July to 2 November 1757; in Capt. Nehemiah Lovewell's company, Col. John Hart's regiment from 27 April to 26 October 1758.

He married Azubah at Hollis, NH, on 30 May 1758 and the date of the marriage falls within his term of service in Col. Hart's regiment. The explanation seems to be that, due to a deficiency of money in the provincial treasury, Col. Hart's regiment was detained within NH until June 1758, so the wedding took place there instead of at the bride's home as was the usual custom.

During the Revolution, he was captain of the Plymouth, NH company of Col. Hobart's regiment and twice in 1777 he led his company into service. He was one of the grantees of Plymouth, NH and one of the exploring party who, before the Charter, visited Plymouth in 1762. He and his father were among the signers of that town's original Charter. In 1764, with the first families to arrive, he came to Plymouth, NH, moving his family there the following year. He was influential in town affairs and was a deacon in the church for sixty-eight years.

John, Jr. and his wife Azubah (Wheeler) Willoughby had twelve children:

• John, b. at Hollis, NH 8 June 1760; m. 29 June 1779 Abigail Davis.
• Josiah, b. at Hollis, NH 9 Feb. 1762; Enlisted 12 March 1777 for the war and assigned to Capt. Benjamin Stone's company, of Col. Scammell's Continental regiment. He died in the service the same year. The town records give October 1777 as the date of death, and the war rolls report his death, 21 Dec. and again, 25 Dec. 1777.
• Azubah, b. at Hollis, NH 17 Oct. 1763; m. 6 Dec. 1781 Thomas Hodge.
• Ebenezer, b. at Plymouth, NH 2 Dec. 1765; m. 1787 Mehitable Mulliken.
• Mary, b. at Plymouth, NH 7 Sept. 1767.
• Abner, b. at Plymouth, NH 14 June 1769; m. 5 Oct. 1797 Jane Stevens.
• Elizabeth, b. at Plymouth, NH 26 April 1771.
• Anna, b. at Plymouth, NH 5 Feb. 1773; m. Moses Mulliken.
• William, b. at Plymouth, NH 6 Nov. 1774; m. 25 July 1793 Jane Kendall.
• Sybel, b. at Plymouth, NH 27 Aug. 1776; m. 22 Dec. 1796 Samuel Lucas of Pummey, VT.
• Josiah, b. at Plymouth, NH 23 Dec. 1778; m. 28 Nov. 1799 Betsey Henman.
• Eunice, b. at Plymouth, NH 8 May 781; m. 2 July 1801 John Morse, son of Daniel Morse.