View from Town Hill in Ipswich MA

Robert and Hannah Pengry Day of Ipswich, and Some of Their Descendants

Posted on by Gordon Harris

*Notes from recent genealogy tours, a work in progress. Please reply below with any additional information or corrections. The featured image above is a 19th-century photo of High Street, taken from Town Hill–GH

The First Three Generations in Ipswich

Robert Day, the settler, was assigned a lot near High St., about where Bialek Park is now, not too far from the Old North Burying Ground. His wife is said to have been Hannah Pengry, the daughter of Aaron Pengry, whose property adjoined theirs. Robert’s son John inherited the homestead, and son Thomas inherited Robert’s farm, farther north on High Street, on the way to Rowley. The family’s relationship to the town of Rowley is evident through several marriages.

Robert Day was about 30 when he migrated to Ipswich in 1635 from Stansted Abbot, England, arriving on the ship Hopewell. In June 1681, he deposed that he was about 77 years old. He became a freeman on 2 June 1641 at Ipswich. He served on several juries; was a selectman in 1658, constable in 1660, and Tythingman in 1678. Robert Day was released from training on 28 Mar 1654 at about 50 years old, a young age to be released from this obligation. His occupation was brickmaker, and behind his house, between High Street and Linebrook Road, was the brickyard.

House lots of the Day Family of Ipswich, MA
The house lot of Robert Day Senior was just north of Lords Square. His wife Hannah, was the daughter of Aaron Pengry, whose lot was nearby. Their children and descendants built homes along High Street, indicating that the family maintained close ties.
House lots on Upper High Street in "Ipswich Village"

Grants of land on Upper High St. from “IPSWICH VILLAGE AND THE OLD ROWLEY ROAD”.

Lot No. 2: This lot, described as “an old Lott containing about nine acres,” about 24 rods wide, was drawn by John Day by his grandfather’s right. Benjamin Dutch, saddler, sold half of it to Joseph Bolles, Dec. 8, 1737.

Lot No. 14: Bounded southeast and south partly by No. 7, partly by Lord’s Little Pasture and partly by Tuttle’s land” was drawn by Alexander Lovell, “the original right of Moses Day,” April 16, 1729 (54:48).

(In 1900, the farm of Mr. Charles Day, formerly the Bradstreet Farm, was reached by Paradise Road.)

Pengry Family

Robert Day’s wife, Hannah Pengry, is believed to have been the daughter of Aaron and Jennet Pengry. Their daughter Hannah was born about 1638, having deposed in 1675 that she was aged about thirty-seven. Two brothers, Moses and Aaron Pengry, both resided in Ipswich by 1641 and were active in town affairs. The surnames of their descendants are alternatively spelled Pingree, Pengre, Pengrey, Pengry, Pingre, Pingrey, and Pingry.

In 1654, Aaron Pengry owned a house lot on High St. near Lord Square, between John Brewer and Mark Quilter. This lot adjoined or was near the lot of Robert Day. Aaron was a tythingman in 1679. In 1652, Richard Scofield, a leather dresser, sold Moses Pengry, yeoman, a house and land, for £17 near the intersection of North Main St. and High St. Here, Deacon Moses Pengry kept an ordinary and dispensed spirits. His son, Moses Pengry (2), was a salt maker, and he built a house beside the Ipswich River, some part of which may have been incorporated in the house still standing at 8 Water St.

John Day, son of Robert and Hannah Pengry Day, married Moses Pengry’s daughter Lydia Pengry in 1664. A financial agreement was made between Robert Day & Hannah, his wife, & Moses Pengry & Lidia, his wife, determining “what each should settle on the children before their marriage.” Among the soldiers fighting in King Philip’s War were four members of the Pengry family: John Pengry, Aaron Pengry, John Pengry, and Moses Pengry.

Robert Day2 and Elizabeth Dresser

Robert Day (2), son of Robert and Hannah Pengry, married Elizabeth Dresser, the daughter of John Dresser Jr. and Martha Thurlow. Robert Day’s farm, which he gave to his son James in his will, was between Ipswich and the Rowley town line. Their neighbor, John Dresser, a cordwainer, had a 66-acre farm, 17 acres of which were in Ipswich; the remainder, including the Dresser homestead, was over the Rowley line. Mark Symonds, John Ayers’ father-in-law, owned an adjoining farm (see map of Ipswich Village below).

John Dresser was one of the company of men and families who joined Ezekiel Rogers when the ship John, of London, sailing from Hull, dropped anchor in Boston in 1638, and the church and settlement in Rowley were established the following year. On Bradford Street in Rowley, John Dresser was assigned a lot containing one Acre and a half, bounded on the South side by Thomas Ellethrop’s house. John Dresser was one of the Rowley selectmen in 1687. In 1692, a new charter was received for the colony, and the General Court, consisting of one hundred and fifty-seven members, first convened under this charter. The Deputies from Rowley were Ezekiel Jewett and John Dresser. The Dresser family is prominent in Rowley’s history over the succeeding centuries.

In 1730, the Ipswich Village folk began their contention to be set off from the old First Parish of Ipswich and annexed to Rowley Parish. In March 1746, Samuel and Daniel Dresser, Purchase and Moses Jewett, Captain Moses Davis, John Harris, and Nathaniel Bradstreet again sought relief, and the General Court, despite the protest of the Ipswich people allowed the estates of these men and the estates of Francis and John Pickard to be annexed to the Rowley First Parish.

Richard Thurlow emigrated from England in 1639 and was one of the first settlers of Rowley, Massachusetts. In 1643, Richard had a two-acre lot in Rowley. Richard and his wife Jane sold their Rowley property in 1651 and moved to Newbury and lived north of the Parker River in the area of the Governor’s Academy. He built a bridge over the Parker River in 1654, and the bridge at that location is still known as Thurlow’s Bridge. On 27 Jan. 1669, Richard and Jane gave part of their farm to their son Thomas, to fall to his son Francis in case Thomas died. Between 1851 and 1871, the ancient house at 2 Neptune St. in Newburyport was purchased by George Thurlow. This property remained in the Thurlow family until the mid-twentieth century.

Thomas Day Sr. & Anne Woodward

Thomas Day (1643-1718) was born in 1642, in Ipswich. His father, Robert Day, was 37 and his mother, Hannah Pengry, was 31. He married Ann Woodward (1651-1718) on 20 October 1672, in Ipswich. They were the parents of at least 2 sons and 5 daughters. He died on 19 March 1718, in Ipswich, at the age of 76. Ann Woodward was the Daughter of Ezekiel Woodward of Wenham, who died in Ipswich.

Thomas Day Jr. & Elizabeth Jewett

Thomas Day, Jr. (1686-1750) married Elizabeth Jewett (1689-1786) on 28 January 1709, in Ipswich. She was the daughter of Jeremiah Jewett of Ipswich and Elizabeth (Kimball) Jewett, who was the daughter of Caleb Kimball and Anna (Hazeltine) Kimball. Sargent Thomas Day was born on 19 June 1686 in Ipswich. His father, Thomas Day, was 44, and his mother, Ann Woodward, was 34. They were the parents of at least 8 sons and 3 daughters. He died on 27 June 1750, in Ipswich at the age of 64.

Jeremiah Day (1712-1765), Son of Thomas Day and Elizabeth (Jewett) Day married Mary Caldwell (1717-1802). Mary Caldwell was the daughter of Nathaniel Caldwell, Born 18 Oct 1669 in Ipswich, the son of John Caldwell and Sarah (Dillingham) Caldwell.  Land was purchased from Jeremiah Day on the north side of the burying ground for £70 by joint action of the two Parishes in 1796. Jeremiah had a son named Jeremiah (1742 – 1825).

James Day and Susanna Ayres

James Day1 was the youngest child of Robert Day and Hannah Pengry. James Day was on the long list of men who took the oath of allegiance to the town in 1678. In Robert Day’s 1683 will, he gave his son John his home, and his son Thomas his farm. To his son James, he wrote, “I do appoint my son James Day to be the sole executor of my last will and testament, to him I give all ye rest of my estate of lands & cattle & goods of all sorts whatsoever and Debts from whosoever due unto him & his heirs forever.” There was no mention of Robert Day’s wife, which tells us that she was deceased.

James Day married Susanna Ayres; her father John Ayres Sr. was a prominent Ipswich resident who promoted the settlement in Quaboag. He was killed in the ambush by the Indians in New Braintree on the same day as the Brookfield massacre. John Ayres’ wife, Susannah Ayres, survived the attack at Brookfield and moved back to Ipswich with her six sons and one daughter. She possessed a house lot in Ipswich in 1678, but the location is unknown. She died on February 8, 1682.

Robert Day was born on 17 Jan 1684 in Ipswich, son of James Day and Susannah Ayres. He married first, Elizabeth Dresser (1686-1730). Together, they had the following (known) children:

  • Mary (Day) Warren (abt. 1707-1747)
  • Susannah (Day) Knight (1712-)
  • James Day (1716-1782). In 1706, a division of land was laid out in a remote section in the northeast section of Windham, CT, which is now included in the township of Hampton in Windham County. The fertile valleys were a favorable site for a settlement, and settlers from Ipswich and other towns in Essex County, MA, soon followed. When James Day (2) moved to Connecticut, he joined several local families who left here looking to obtain land. In December 1716, the residents requested “that the northeast part be a parish.” (now the town of Hampton). James Day married Mary Parkhurst after he moved to Connecticut.

Aaron Day (1783-1862) was born on 2 July 1783 in Ipswich, son of John and Eunice Day. He married Martha Tibbetts (1777-1844) on 9 September 1806, in Embden, Somerset, Maine, and died in Maine. Aaron Day’s house was located within sight of the Old North Burying Ground. Thomas Franklin Waters wrote, “The spot now occupied by the Payne School house is remembered by our old citizens as a knoll or small hill, on which a small house stood, near the front fence of the schoolyard.

John Day, Jr. (1750-1820) married Sarah Goodhue Day (1751-1845) on 22 December 1774, in Ipswich. Sarah was the daughter of Aaron Day and Sarah Goodhue. John Day was born on 24 February 1750 in Ipswich. His father, Jeremiah Day, was 37, and his mother, Mary Elisabeth Caldwell, was 32. Aaron and Jeremiah were his brothers. They were parents of at least 5 sons and 2 daughters. He died on 12 October 1820, in Winthrop, Kennebec, Maine, age of 70. Sarah Goodhue Day’s gravestone is at the Old North Burying Ground. Daughter of Francis Goodhue Sr. and Sarah (Fowler) Goodhue.

The oldest part of the Day-Dodge House at 57 North Main Street was the home of Nathaniel Day (John2, John, Robert1) and Sarah Pengry Day, born December 5, 1700, who died in 1740. His widow, Elizabeth, married Col. Isaac Dodge, who served as a member of the Committee of Correspondence and Safety during the Revolutionary War.

Old North Burying Ground, High St., Ipswich

E-71 In memory of Mr. Aaron Day who departed this life Aug. 24th, 1790; In the 64th year of his age. Lord, we adore the vast designs, Th’ obscure abyss of providence! Too deep to sound with mortal lines too dark to view with feeble sense. (F.S.) Mr. Aaron Day., Day, Aaron

E-23 In memory of Mr. Nathaniel Day who died Feb. 1st, A.D. 1740, in the 40th year of his age. In memory of Mrs. Elizabeth Day, relict of Mr. Nathaniel Day, who died March 28th, A.D. 1772, in the 68th year of her age. “Inactive in the damp and gloomy Grave, beneath this stone, to worms a prey, we sleep,” Unconscious of the world, and all her woes. (F.S.) Mr. Nathaniel Day. Mrs. Elizabeth Day., Day, Nathaniel

E-72 In memory of Mrs. Sarah Day, wife of Mr. Aaron Day, the daughter of Capt. Frances Goodhue: who departed this Life July 25th, 1783, in the 51st year of her age. Behold and see as you pass by, as you are now so once was I; as I am now so must you be, prepare for death and follow me. (F.S.) Mrs. Sarah Day., Day, Sarah Day

C-7 – Here lyes buried the body of Ensign John Pengry dec’d. Aug’t. the 22nd, 1732, in the 49th year of his age. (F. S.) John Pengry; Ensign John Pengry 1684 – 22 Aug 1732

Old Rowley Burying Ground

  • Aaron Pengry, Born 1652 in Ipswich. Died 19 Sep 1714 (aged 61–62)
  • Dr. Amos Dresser 9 May 1713 – 22 Sep 1741
  • Elisabeth Dresser 9 Dec 1716 – 20 May 1736
  • Mary Leaver Dresser 1 Sep 1649 – 21 Aug 1714
  • Samuel Dresser 10 Feb 1643 – 28 Dec 1704

Sources and Further Information

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