I have one reference for a John Bole at Mohill in South co. Leitrim from 1727 ref. and Griffiths Valuation of 1856 lists a John Boles at Ballinamore ref. and a James Boles at Gortnacorkage ref. but the only significant documented Bowles presence that I have so far was a Boles family in the Fingreagh area.
The Boles of Fingreagh appear to have come from co. Fermanagh.The Poll of Electors for co. Fermanagh in 1788 ref. includes: Surname Given Name Abodes Freeholds Bowles Alexander Fingreagh Derngogh
This documents that Alexander Bowles was living in Fingreagh, co. Leitrim by 1788 while holding a significant value of land in Derngogh, co. Fermanagh. The Boles had been at Dornogagh, co. Fermanagh since much earlier. See the Bowles of Fermanagh.
A further sign of a connection between Dornogagh and the Boles of Leitrim is their use of given names. 'Alexander' is seen frequently in both but while not common it isn't enough indication in itself. However, 'Bennet' would have to be considered an unusual given name and the earliest reference that we have for a Boles in Dornogagh, Fermanagh is a Bennet Boles who registered a freehold there in 1749 and later there was a Bennet Boles listed in the Leitrim Militia in 1797. ref.
A deed of assignment dated 1803 refers to a Francis Bowls, father Edward Bowls, deceased, and mother Anne Bowls nee Buchanan, at Fingreagh. A list of diocesan Wills lists Francis Boles of Fingraugh as having died in 1817. The Rent Books for Fingreagh in 1846 list Ed., E. and Edward Jervis Bowles as farming at Fingreagh.
That is possibly a direct line of descent from Alexander, to Edward, to Francis and to Edward Jervis but there may well have been additional male lines added along the way and no records have yet been found to help sort that out. The family connection cannot be denied in any case.
We do have a fairly reliable family tree for the Edward Jervis Boles line, see below.The 1856 Griffith's Valuation of co. Leitrim includes the following in Inishmagrath parish: (note: the area is given in acres, rods & perches, and the values are in pounds, shillings and pence) Lot Occupier Immediate Desc. Area Land Bldg. Lessor a r p Value Value Fingreagh Lower 1 Edward Bowles William Johnston House, offices, land 20 1 3 8 10 0 0 5 0 2 Andrew Bowles same Land 2 3 23 1 10 0 - 3 Andrew Bowles same House, land 11 3 33 5 10 0 0 5 0 4 Ed. Bowles Jr. same House, offices, land 17 3 16 6 15 0 0 5 0 Fingreagh Upper 6a John Bowles William Johnston House, offices, land 36 1 33 9 0 0 0 5 0 8 Edward Bowles same land 21 2 23 8 15 0 - 9a Barbara Bowles same House, offices, land 81 0 10 25 5 0 0 10 0 Greaghnaglogh 19 George Bowles Hugh,Lyons, House, offices, land 18 2 20 7 0 0 0 15 0 Montgomery
A Partial Family Tree of the Boles of Fingreagh, co. LeitrimEdward Jervis Boles b. ~ 1798 m. Barbara Crawford ~ 1819 1. James Boles b. ~ 1820 m. Jane Payne Aug. 14, 1854 Killargue, co. Leitrim 1.1 Edward Boles b. 1857 (of Clooneen, co. Leitrim) 1.2 James Boles b. ~ 1861 co. Leitrim ( a merchant on Duncarin Street, Belfast and later in Thurles, co. Tipperary) m. Lucy Dorothy ? (b. ~ 1862 co. Wexford) 1.2.1 James W. Boles b. ~ 1895 Belfast 1.2.2 William R. D. Boles b. ~ 1896 Belfast, co. Antrim 1.2.3 Jane Lucinda Sarah Boles b. Oct-Dec, 1897 co. Tipperary 1.2.4 Mabel Beatrice Boles b. Apr-June, 1899 co. Tipperary 1.2.5 Benjamin Jones Boles b. July-Sept. 1902 Thurles, co. Tipperary Benjamin d. Apr. 2, 1931 (aged 28) Thurles, co. Tipperary Lucy d. Aug. 24, 1902 Thurles, co. Tipperary James d. Oct. 21, 1930 (aged 70) Thurles, co. Tipperary (only William was at home with father James in 1911 Census; James Jr. was visiting Semple family in Farranrory, co. Tipp; Lucy, Mabel and Benjamin (age 8) were living with Uncle and Aunt, William and Mary Plummer in Ballybrannis, co. Wexford) See The Boles of Fingreagh in Tipperary for more on this family 1.3 John Boles b. May 1, 1865 Drumkeeran, co. Leitrim d. Oct.-Dec. 1880 (Manorhamilton Reg. Dist) 1.4 Alexander Boles b. ~ 1866 Lisdrumgran, co. Leitrim (father: James Boles) (of Knock Farm, Rathdowney townland near Abbeyleix, Queens county) m. Susan Pearson (b. ~ 1868 Queen's county) June 19, 1894, Abbeyleix (Marriages Index, Ireland 3, 279; Methodist Church Register ref.) 1.4.1 Edith Susan b. ~ 1896 Queen's county 1.4.2 Evelyn Jane b. July-Sept., 1898 Abbeyleix, Queen's county (Births Index, Ireland 3, 251) 1.4.3 Herbert James b. July-Sept., 1900 Abbeyleix, Queen's county (Births Index, Ireland 3, 261) 1.4.4 Marjorie D. b. ~ 1901 Queen's county 1.4.5 Violet Francis b. ~ 1904 Queen's county See The Boles of Abbeyleix, co. Laois for more on this family. 1.5 William Boles b. Nov. 18, 1867 Drumkeeran, co. Leitrim (of Lisdrumgran, co. Leitrim) 1.6 Benjamin Boles b. Feb. 28, 1871 Drumkeeran, co. Leitrim (later of Roscrea, co. Tipperary, merchant) 1.7 Robert Boles (of Boyle, co. Roscommon, merchant) 1.8 Jane Boles m. William S. Pearson (of Rathdowney, Queens county) James d. ~ 1893 2. Alexander b. 1831 m. Margaret Crosswell (John) Jan. 22, 1857 Cloonclare, co. Leitrim 2.1 Barbara d. as infant 2.2 Barbara d. young 2.3 Edward b. 1861 m. Catherine Trotter ~ 1893 2.3.1 Margaret b. 1898 m. Robert Lindsay 2.3.2 Alexander b. 1899 m. Frances Bracken 2.3.3 Elizabeth m. Tom Trotter 2.4 Catherine Anne b. 1862 m. John Stewart Jan.-Mar. 1884 Manorhamilton Reg. Dist. Catherine Anne d. Jan.-Mar. 1929 Manorhamilton Reg. Dist. 2.5 James b. 1863 (in RIC, died accidentally in fall from a horse in 1913) 2.6 Isabella b. Apr. 5, 1865 m. Mr. Elkins 2.7 Margaret b. Jan. 17, 1867 (did not marry) 2.8 Mary Jane b. Mar. 25, 1869 Drumkeeran, co. Leitrim 2.9 Alexander b. Nov. 4, 1870 Drumkeeran, co. Leitrim (moved to Boston and changed name to Bolles by deed poll) 2.10 Thomas b. Nov. 20, 1872 co. Leitrim (did not marry) 2.11 Irwin b. Oct. 3, 1874 Fingreagh, Innismagrath, co. Leitrim 2.12 George Boles b. Aug. 12, 1876 co. Leitrim Alexander d. 1907 3. Anne m. John Mullen 1856 4. Mary Jane m. ? Edward d. 1850 Barbara d. ~ 1863 The following two lines should connect up to the above line possibly a few generations back: Edward Boles m. ? 1. James Boles m. Margaret McMaster Oct. 8, 1866 Kilmactraney, co. Sligo 1.1 Edward b. Jan. 15, 1868 Drumkeeran, co. Leitrim 1.2 Mary Ann b. Oct. 10, 1869 Drumkeeran, co. Leitrim 1.3 Margaret b. May 22, 1871 Drumkeeran, co. Leitrim 1.4 Robert b. 1873 1.5 John James Boles b. Nov. 14, 1875 co. Leitrim d. July-Sept. 1884 Manorhamilton Reg. Dist. (age 9) 1.6 Eliza Jane b. Sept. 18, 1878 Fingreagh, co. Leitrim 1.7 William b. 1882 1.8 Irwin b. Apr.-June 1884 Manorhamilton Reg. Dist. (parents and son Robert still at Fingreagh Lower in 1901 Census) James Boles m. Catherine Dolan 1. Bridget b. Dec. 19, 1864 Dromahair, co. Leitrim The Boles of Fingreagh, co. Leitrim were the origin of the following lines: Alexander Boles of Abbeyleix Two Boles brothers who settled in Tipperary, James Boles, a draper in Thurles and Benjamin Boles in Roscrea The Boles of Boyle, co. Roscommon (that page is under construction but see their website) The Boles Chemists in Dublin (TBA)