The northern tip of New York state borders the area of southern Ontario where many English and Irish immigrants were settled in the early 1800’s as a defense against any possible repeat of the US invasion of Canada which had occurred in 1812.  In the mid-1800’s many of these settlers moved across the border and settled in northern New York State.

The 1860 and later Census records for this area show a significant percentage of people having been born in Canada and with their parents born in Ireland or England.  Some of these were Bowles.

The Bowles of Naples, Ontario, New York State

James Boles and Jane Clindenen were married in Ireland in 1829 and shortly afterwards emigrated to Canada.  They were probably from northern Ireland as they were Presbyterian, which was much more common in the north, and the family later adopted the Boals spelling of their name which we also connect with the northern lines.  The Clindenen name (spelling variations: from Clendinen to Glendenning) is clearly Scottish and generally appears in Ireland in only the north, particularly in counties Antrim, Armagh and Down.

The couple were certainly in Canada from about 1832 until 1839 where three children were born.  This was most likely in the St. Catharines, Lincoln co. area near the US border at Niagara Falls and only about 150 miles from Naples, NY where we find them later.  During those years there were a large family of Boles from Armagh, Ireland living at  St. Catharines including a James Boles of an appropriate age but that James remained there until his death in 1852.  Likely he was a cousin of 'our' James.  A newly married couple would be more likely to follow the lead of other family members who had previously emigrated than to head off completely on their own.  Boles is not a common name but the most convincing argument for St. Catharine's is that the very uncommon name Clendennan is also found there in that timeframe.  The local newspaper reported in 1826 that a Jonathan Huston Clendennan had acquired and laid out several town lots which were for sale in St. Catharine's. ref.  There is also an 1867 article which mentions both Boles and Clendennan as having arrived in the St. Catharine's area in the early 1820's.  ref. 

 In 1900 the Naples News refers to Hugh Bolles and Samuel Boals as living in Hickory Bottom and John Boals in Naples.  Samuel Boals was still at Hickory Bottom in 1907.  The Jan. 1, 1908 paper reports that he has sold the farm.