There were two William MONTGOMERY families in the Shackle Island community in the early years of settlement. It is not known if they were related or if the families originated in the same place before crossing the mountains to the Cumberland Country. The William MONTGOMERY who built Old Brick arrived in Sumner County in about 1782 from Pennsylvania. He was a surveyor, and through that endeavor he increased his original grant of 640 acres to over 6,000 acres. His will dated 30 Jun 1835, "now in 73rd year of age." reveals that his wife was named Jane, and other sources report her surname was McMillan. Their children were Daniel who married Sally GARRISON, Margaret M. who married William M. BELL, Jane who married John SIMPSON, Hannah who married first Dr. John PRIESTLY and second Beverly NELSON, John who married Jane FARRAR, Robert, Elizabeth who married William RAULSTON, William J., Mary, and Jefferson Thomas who married Polly JOUETT.

William MONTGOMERY the Surveyor built Old Brick near the present day intersection of Long Hollow Pike and Shackle Island Road. William MONTGOMERY who is the subject of this family history built his home about three miles south of that intersection on what is today Callender Lane, and it is there where he and many of his descendnats are buried.

William Montgomery and His Descendants
Generation No. 1

1.  WILLIAM1 MONTGOMERY  was born 22 Jul 1743 and died 10 Jan 1819 in Sumner Co
TN.  It is believed that his wife's name was MARGARET, but her tombstone is illegible.

Children of WILLIAM MONTGOMERY and MARGARET are:
     i.    ROBERT MONTGOMERY, b. Abt. 1772; d. Apr 1788, Sumner Co TN.
     ii.   JOHN MONTGOMERY, b. Abt. 1774; d. Apr 1788, Sumner Co TN.
     iii.  THOMAS MONTGOMERY b. Abt. 1778; d. Apr 1788, Sumner Co TN.
2    iv. WILLIAM MONTGOMERY, JR, b. 15 Apr 1784; d. 14 Oct 1870, Sumner Co TN.
3.   v.  SARAH "SALLY" MONTGOMERY, b. Abt. 1790; d. Aft. 1845.
     vi.  MARGARETTE/MARGARET MONTGOMERY, b. Bef. 1800; m. GEORGE MARTIN
     on 6 Mar 1819 in Sumner Co. TN.
     vii. MARY MONTGOMERY, b. Bet. 1800 - 1810; d. Bef. 1840; m. ANDREW
           MARTIN, 26 Aug 1812, Sumner Co., TN.
     viii  NANCY MONTGOMERY, b. Bet. 1800 - 1810; m. JAMES WRIGHT, 04 Dec 1812,
           Sumner Co., TN.

Will of William Montgomery, the elder
Signed 9-Jan-1819
Recorded Feb-1819
Source: Will Book I, pages 289-290 (TSLA Microfilm)
In the name of God Amen: I William MONTGOMERY Sr. of the County of Sumner and State of Tennessee being weak in body but sound in mind & memory and calling to mind that it is appointed for all mankind once to die, do make and affirm this to be my last will and Testament first of all I commend I soul to God who gave it and my body to the Earth from whence it came, to be buried in a decent Christian like manner and my property I dispose of in the following manner, to wit, To my son William MONTGOMERY Jr. I give and bequeath one negro man named Randal one Negro woman named Betsy and one Negro boy named Allan and also two small Negro girls named Hannah and Nancy. Also one desk and one table one feather bed and one kettle. To my daughter Margarette MONTGOMERY I give and bequeath one Negro man named Neal one negro boy named Joe and one negro boy named Elmore and one negro girl named Harriett, also one dark bay horse one (buffet?) and one table one large and one small kettle. I also give and bequeath to my son William MONTGOMERY and my daughter Margaret MONTGOMERY all my stock of cattle sheep and hogs as they are now divided between one wagon & all my farming utensils and all my household and kitchen furniture not here before mentioned to be equally divided between them the said William and Margaret MONTGOMERY. To my daughter Sally WATKINS I give and bequeath one hundred dollars to be paid here by Mary MARTIN and Nancy WRIGHT fifty dollars each. To my daughter Mary MARTIN I lend during her material life one negro man named Charles and one negro girl named Mariah and give and bequeath the said Charles and Maria and her increase after her death to the lawful heirs of her body out of the loan of which said negroes she shall pay Sally WATKINS fifty dollars. To my daughter Nancy WRIGHT I loan during her natural life one negre woman named Judah and one negro boy named Charles and I give and bequeath after her death the said Judah and Charles and their issue to the lawful heirs of her body out of which said loan she shall pay Sally WATKINS fifty dollars. And for the management of my estate after my death I do appoint my son William MONTGOMERY Executor thereunto and thereby disannul all former wills whatever and disclose this to be my last will and testament given under my hand and seal this ninth day of January in the year of our Lord one thousand eight hundred and nineteen.
his
mark
William MONTGOMERY
Attest
Zack TALLEY Jr.
George MARTIN

Extracted From Early History of Middle Tennessee
By Edward Albright, 1909, Chapter 30
During the month of April (1788) the three sons of William MONTGOMERY, John, Robert and Thomas, were killed near their father's house, on Drake's Creek, three miles below Shackle Island. John, the eldest boy, had suffered a broken thigh at the hands of the Indians a year before and was still on crutches. On this occasion he had hobbled out into the orchard where his brothers were trimming apple trees. The Indians rushed out from a neighboring thicket and ruthlessly murdered and scalped the three, leaving their bodies in a heap on a brush pile.

2.  WILLIAM MONTGOMERY, JR (WILLIAM1) was born 15 Apr 1784, and died 14 Oct 1870
in Sumner Co TN.  He married MARY "POLLY" MARTIN 16 Sep 1816 in Sumner Co., TN .

Child of WILLIAM MONTGOMERY and MARY MARTIN is:
     i.   WILLIAM3 MONTGOMERY, JR, b. 07 Oct 1819; d. 18 Sep 1876, Sumner Co TN.

3.  SARAH "SALLY"2 MONTGOMERY (WILLIAM1) was born Abt. 1790, and died Aft.
1845.  She married ROBERT WATKINS.

Children of SARAH MONTGOMERY and ROBERT WATKINS are:
4.   i.   EMILY WATKINS, b. Abt. 1815.
5.   ii.  JAMES WATKINS, b. Abt. 1819, TN.
     iii. MARGARET WATKINS, m. ROBERT BOYD, Bet. 5 Apr 1820 - 1826, Sumner Co., TN.
     iv.  MARTHA WATKINS, m. MARMADUKE LAY, 05 Dec 1826, Sumner Co, TN.
     v.   MARY WATKINS, m. DEMPSEY COOK.
6.  vi.  NANCY WATKINS, d. Bef. 27 Oct 1845.
     vii. PHILIP WATKINS, m. ELIZA LAY, 13 Oct 1823, Sumner Co, TN.
     viii.WILLIAM WATKINS.
7.   ix. SARAH ANN WATKINS, b. 06 Feb 1821, TN; d. Abt. 1900, Sumner Co, TN.

Generation No. 3

4.  EMILY3 WATKINS (SARAH "SALLY"2 MONTGOMERY, WILLIAM1) was born Abt.
1815.  She married JOSEPH L. GRAY.

5.  JAMES3 WATKINS (SARAH "SALLY"2 MONTGOMERY, WILLIAM1) was born Abt.
1819 in TN. He married ADALINE

Children of JAMES WATKINS and ADALINE are:
     i.   MARGARET T.4 WATKINS, b. Abt. 1858.
     ii.  PHILIP K. WATKINS, b. Abt. 1860.

6.  NANCY WATKINS (SARAH "SALLY"2 MONTGOMERY, WILLIAM1) died Bef. 27 Oct
1845.  She married JOHN LAY 24 Sep 1829 in Sumner Co., TN.

Children of NANCY4 WATKINS and JOHN LAY are:
     i.   WILLIAM THOMAS4 LAY
     ii.  JOHN SUMNER LAY
     iii. ELIZA ANN LAY
     iv.  MARY JANE LAY

7.  SARAH ANN3 WATKINS (SARAH "SALLY"2 MONTGOMERY, WILLIAM1) was born
06 Feb 1821 in TN, and died Abt. 1900 in Sumner Co, TN   She married ALBERT G. DUGGER
03 Apr 1841 in Sumner Co, TN, son of FLOOD DUGGER and MARY BRUCE.
(For more information see the Dugger Family)