Hi Lauren,
There is a gap in your Dibble family history during the War of 1812 and you do not appear to have researched records from that event. There is a slight possibility that those records may reveal more about the Dibble and Diamond families. All men between the ages of 16 and 60 were required to report for militia duty by law. The militia records therefore list who was living in each township between 1812 and 1815.
As Oren Dibble was about 19 years old in 1812, his name may appear in the militia rolls and related documents. His father and brothers may have served as well. If we assume that Oren was living in the area of Fredericksburgh at that time, he probably would have served in the Addington or Lennox Militias. Even though the counties were amalgamated in 1800 they had separate militia regiments in 1812.
In June, 1812, each regiment was to form about 2 flank companies of young men who were able to serve for extended periods of time. They received special training to engage the Americans in combat. I did not find the Dibble surname in those records but did find:
Private Marcus Diamond, Lennox Militia, page 68
Private Jacob Diamond, Addington Militia, page 63, “died during service”
After the war both men received a militia land grant. The average of a flanker was 25. Do you want that information that would tell you the township or county that they were living in after the war?
There may have been an additional 8 companies in each regiment which served for brief periods of time. I did not search those rolls as it would take hours to review hundreds of pages. If you want to take on that task, I can send you links to the online rolls.
After the war, Upper Canadians who suffered personal losses could make a petition for reimbursement. The Diamond and Dibble surnames were not in those records and there were only a few claims from Fredericksburgh.
My research website is online at
https://warof1812cdnstories.blogspot.com/
My War of 1812 research guides are at the bottom of the right-hand column.
Questions are welcome. Wishing you well,
Fred Blair