Welcome! I really enjoy exchanging information with people and love that this blog helps with that. I consider much of my research as a work in progress, so please let me know if you have conflicting information. Some of the surnames I'm researching:

Many old Cape families including Kelley, Eldredge/idge, Howes, Baker, Mayo, Bangs, Snow, Chase, Ryder/Rider, Freeman, Cole, Sears, Wixon, Nickerson.
Many old Plymouth County families including Washburn, Bumpus, Lucas, Cobb, Benson.
Johnson (England to MA)
Corey (Correia?) (Azores to MA)
Booth, Jones, Taylor, Heatherington (N. Ireland to Quebec)
O'Connor (Ireland to MA)
My male Mayflower ancestors (only first two have been submitted/approved by the Mayflower Society):
Francis Cooke, William Brewster, George Soule, Isaac Allerton, John Billington, Richard Warren, Peter Browne, Francis Eaton, Samuel Fuller, James Chilton, John Tilley, Stephen Hopkins, and John Howland.
Female Mayflower ancestors: Mary Norris Allerton, Eleanor Billington, Mary Brewster, Mrs. James Chilton, Sarah Eaton, and Joan Hurst Tilley.
Child Mayflower ancestors: Giles Hopkins, (possibly) Constance Hopkins, Mary Allerton, Francis Billington, Love Brewster, Mary Chilton, Samuel Eaton, and Elizabeth Tilley.

Friday, March 24, 2023

Isaac Pepper, born Roxbury 1659, m. Apphia Freeman, died Eastman before July 1740


Isaac Pepper was born 26 April 1659 at Roxbury, Suffolk County, Massachusetts, to Robert and Elizabeth (Johnson) Pepper. He was baptized there on 1 May 1661. Isaac is my 10th great-grandfather on my grandmother Milly (Booth) Rollins’ side of the family.  I wrote about his parents here.

Isaac was one the early settlers at Eastham, Barnstable County, Massachusetts, living there prior to 1675. He became the schoolmaster, replacing Jonathan Sparrow, indicating he was educated.  (A History of Early Orleans pg. 34)

Isaac married Apphia Freeman at Eastham on 7 October 1685. Apphia was born 1 January 1666 at Plymouth, the daughter of Samuel and Mercy (Southworth) Freeman. 

The children of Isaac and Apphia, recorded Eastham:

i. Apphia Pepper born 24 February 1687; married Timothy Cole; died 6 April 1718 at Eastham

ii. Mercy or Mary born 7 August 1690; married William Freeman, 16 October 1711 

iii. Isaac born  29 July 1693,  m. Elizabeth Freeman

iv. Robert born 15 February 1695/6l m. Mary Snow

v. Elizabeth born 11 July 1698; m. Robert Young

vi. Joseph born 1 November 1700, died 1 May 1703

vii. Solomon born 15 January 1703; m. Phebe Paine 

viii. Joseph was born  24 February 1704/5

I descend from Apphia who married Timothy Cole on 2 November 1709, at Eastham. 

Isaac and Apphia settled in the lower portion of Eastham which in 1696 separated into the town of Harwich. 

May 1710 Issac Pepper was appointed to enforce the whaling regulation of Eastham.  He was to collect a fee from the whalers who caught them near the shore.  He was to keep one-fourth of the fees collected, but it is unknown how successful it was since it was discontinued a few years later.  (History of Billingsgate pg. 96-97)

Mr. Isaac Pepper and Captain Samuel Freeman were on the committee at Eastham to lay out 24 parcels of land at Billingsgate (later Wellfleet)  in the 1711 Eastham land division. Settlers as well as Indians already at Billingsgate petitioned to stop the land grants since they used the land, its timber, and other resources for themselves.  

In 1722 Isaac Pepper along with John Paine and Samuel Knowles where appointed to a committee to hear why the community of Billingsgate should establish its own town government. That same year the General Court of Massachusetts allowed the community to separate from Eastham owing to the difficulty of the church members to attend church at Eastham.  (History of Billingsgate, pg. 40)

Isaac was named first in his father Robert Pepper’s 4 July 1684 will, to receive the lot in the Pond Plain and a lot at Ainsworth Hill together with four acres of salt marsh next to John Ruggles’ marsh. Isaac and Jacob to divide the 21.5 acre wood lot their father received in the third division of lands in Roxbury; Isaac to have the half next to Dedham and Jacob the half next to Roxbury. If Isaac decides to sell the land, he is to offer it first to his brother Jacob. Isaac is to pay his sister Elizabeth Everett of Dedham twenty pounds in money or in cattle, five pounds each year over four years. Isaac and Jacob to make payments to the two schools at Roxbury. Jacob was to receive his father’s house, barn, orchard, and meadow. Isaac was Robert and Elizabeth’s sixth son; all of his older brother’s pre-deceased him. 

Isaac served as a selectman and frequently witnessed his neighbor’s wills, acted as an estate administrator, and conducted estate inventories, indicating he was an important and respected member of the community. He is, at times, referred to as Gentleman in records. 

  • On April 15 1697 Isaac Pepper was listed as an administrator of the estate of Richard Rich who died in 1692, written as both Pepper and Piper in the documents. He and Richard Rich conducted the inventory and Isaac Pepper is listed as being owed 1 pound 8 shillings from the estate. (BcPR 2:39)
  • On 18 July 1700, Isaac Pepper took the inventory of Mrs. Mary Smith. (BcPR 2:181)
  • 15 August 1702 Isaac Pepper was one of the men who conducted the inventory of the estate of Thomas Crosby of Harwich. (BcPR 2:118)
  • In 1712 Isaac Pepper, gentleman, was appointed as administrator of his father-in-law Samuel Freeman’s estate. Samuel is referred to as a deacon from Eastham.
  • Isaac Pepper presented Samuel Freeman’s inventory to the Probate Court at Barnstable 29 January 1712/13. (BcPR 3:108)
  • Isaac Pepper witnessed Stephen Atwood’s 20 May 1715 will. Made oath to this on 12 July 1722.  (BcPR 4:64)
  • 10 August 1715, Isaac Pepper witnessed the will of Nathaniel Mayo of Eastham. (BcPR 3:306)
  • Isaac Pepper witnessed the will of George Brown of Eastham, 29 June 1721. He was also one of the men who took Brown’s estate inventory 24 July 1721. (BcPR 4:213)

I’ve seen other researchers give Isaac’s death as 1704 and Apphia’s as 1705 but without sources. This seems improbable as Apphia and some of her children and grandchildren signed an agreement to the settlement of Isaac’s estate on 29 July 1740, so Isaac would have died closer to that date.  

The agreement of the heirs of Isaac Pepper [Sr.] of Eastham, yeoman, dated 29 July 1740, was signed by:

the mark of [widow] Apphia Pepper

son Isaac Pepper (administrator)

Son Robert Pepper (who received land where he lived near Indian Brook)

Son Solomon Pepper 

Son Joseph Pepper

Isaac Cole, son of daughter Apphia Cole, deceased

Granddaughter Dorothy Freeman (by mark) and her husband Thomas Freeman of Harwich

Granddaughter Susan Brown (by mark) and her husband Joseph Brown of Eastham

Children of deceased daughter Apphia (Pepper) Cole

Daughter Mercy Freeman wife of William Freeman of Harwich (by mark) 

Daughter Elizabeth Young (her mark) and her husband Robert Young Jr of Eastham

Witnesses: Nathaniel Snow (his mark), Hannah Remick (her mark), Seth Knowles and Desire Doane (her mark) the settlement was acknowledged 6 July 1743, by all but widow Apphia Freeman Pepper and Joseph Brown


Torrey’s New England Marriages to 1700

Durand Echeverria, History of Billingsgate, 1991, pg. 35-36

David Hamblin, NEHGR, “The First Settlers of Eastham, Mass.,”  vol. 6, Jan 1852

Barbara Lambert Merick (compiled by), William Brewster of the Mayflower and the Fifth Generation Descendants of his Daughter Patience, GSMD’s Mayflower Families in Progress, 2001, p 73

Emily Clark Landon, Pepper Genealogy: Ancestors and Descendants of Robert Pepper of Roxbury, Mass., Angola, NY, 1932

Ruth Barnard, A History of Early Orleans, Orleans, Massachusetts, 1975 

Barbara Lambert Merrick, Mayflower Families in Progress William Brewster, published by GSMD, 2014