Family History Friday

No offense to my Canadian friends and neighbors but Canada feels like the black hole of family history. So many trails lead back to Canada and then the path evaporates. I've been reading and brainstorming and thought I'd share where we are in the process.

Potential ways the ODoyle, Flagg and Cain families came to be in the Prescott, Ontario area in the late 1700s

source

• they could have been British loyalist relocating after the Revolutionary War
• they could have been indentured servants of the above group
• the men could have been part of the Irish Brigade
"The Irish Brigade sailed from the French harbor of Brest May 3, 1755. There were two regiments in the fleet. They were stationed in what is now Kingston, Ontario and on the frontier of Lake Champlain. The Irish Brigade fought the British near Fort Oswego unsuccessfully and then captured the Fort in 1756. One Irish regimental unit, with red uniforms and green facings, was seen to have participated in the siege of Fort Oswego. Later the Irish Brigade captured Fort William Henry, which was a terrible defeat for the British. On July 8, 1758, the Irish Brigade defeated the British at Fort Ticonderoga. That was three major defeats for the British. Many of the French officers wounded in the Battle of Ticonderoga (or Carrillon as the French called it) had Irish surnames. The Irish Brigade was also stationed in the Ohio River valley at Fort Duquesne at this time and at Fort Chartres in Illinois. (4) At the surrender of Montreal, it is thought that the French regimental colors were not turned over to the English because they were in fact those of the Irish Brigade, whose members might be subject to the charge of treason. No Irishmen were among the surrendered soldiers at Montreal who returned to France aboard English vessels and it appears that many of the Irish Brigade blended in with the French-Canadian populace of Montreal."
• regular immigrants 
• mystery option 4 (there's always something I haven't come across or discovered yet)

The rest of the Irish-Canadians are more of a mystery since we're not really sure when they arrived or where exactly in Canada they lived. All were in the US by 1880. Since all my Canadian relatives arrived at some point from Ireland here are some pages I'm reading in hopes of learning more:

Irish-Canadian History
Our expert answers a question about tracing Irish immigrants to Canada