When it comes to the first-born son of Henry Ouderkirk and Sarah Eliza Casselman, researcher and author Shirley Forth and I have come to different conclusions. According to Shirley, John Benjamin Ouderkirk was known as John Alonzo Ouderkirk, born about 1850 in St. Lawrence County in New York state. Shirley recorded the wife of John Alonzo as a Malinda Ouderkirk and they made their way west with their children to Illinois. I do not believe this couple belonged in the immediate family of Henry Ouderkirk.
On the 1851/2 Census for Henry, John B. Ouderkirk was listed as age 3, so he was born about 1849. On the 1861 Census, Benjamin Ouderkirk was recorded, age 11, so born about 1850 in Upper Canada and on the 1871 Census he was listed as John, age 21, so born about 1850 in Ontario.
I did find a birth record for a Constance Blanche (Amelia) Ouderkirk, born.May 28, 1879, in Muskoka. Her parents were listed as John Benjamin Ouderkirk and Caroline Keeler, although the transcription of same appears as John Benjamin Outerkirk and Caroline Heeler. As we know from land records that Henry brought his third family to Muskoka about 1873, it seems most likely that John Benjamin Ouderkirk was indeed John B. Ouderkirk, Henry and Eliza's son.
On the 1881 Census, John Ouderkirk was recorded living in Monck Township and working as a carpenter. He was living with his wife, Caroline, and children – eight-year-old twins John and Carrie, six-year-old Mallie, three-year old Annette and two-year old Constance.
I have been unable to locate any other references to John’s twin, Carrie, after the 1881 Census. On February 16, 1891, John’s daughter Mildred Mabelle (Mallie) married William Clarence Gilkes. The Gilkes family eventually moved to Newmarket, Ontario.
Caroline Ouderkirk and her children John, Netty (Annette) and Constance were listed in the 1901 Census for Monck with Caroline as the head and a widow. It is presumed that John died sometime after 1881. I cannot locate an 1891 census for this family. However, I have found a City Directory for Bracebridge for 1896 which listed Caroline as Mrs. John Ouderkirk, a freeholder on Lot 1 Concession I in Monck Township. There was no listing for John so presumably he had died before 1896.
In a local history book Raw Life, by J. Patrick Boyer, on pages 317 and 318, Blanche (also known as Constance) and Caroline were sworn to testify in a court case of Mary Ann Prentiss v John Ouderkirk (Jr) on January 4,1895. As John's father did not testify, I believe he had passed away already, so his death was likely between April 4, 1881, and December of 1894.
The court case against John Jr. was “For malicious injury to a certain sleigh, the property of James Prentiss.” John pleaded not guilty. James Prentiss was seven years old and his mother, Mary Ann Prentiss, had testified that she had bought the sleigh, and it was broken beyond repair by John when he picked it up and smashed it to the ground. She wanted John to pay for it. John said he wouldn’t, but it may have had something to do with a dog that had been tied to the sleigh. John, his mother, and sister testified that the dog was his. How it became attached to the sleigh was not explained in the court case. John was found guilty and ordered to pay 50 cents as a fine, 50 cents in damages and costs of $2.75.
In 1908, Caroline’s daughter Carrie, aged 26, married William Kitchell in Independence, Missouri. In 1909, Caroline and her son, John, and daughter, Constance, moved to Kansas City, Missouri. Caroline's daughter Annette, aka Nettie or Netty, had moved there in 1903, however, she appeared with her uncle, George Ouderkirk, on the 1905 Iowa Census for Pottawatomie. Perhaps she was just there visiting because Caroline, John, Annette, and Blanche appeared together on the 1910 Census for Kansas City.
On the 1915 City Directory for Kansas City, Caroline A. Ouderkirk was listed as the widow of John B. Ouderkirk living at the New York Apartments in Kansas City. Also listed at that address were Annette A. (bookkeeper), Blanche C. (stenographer), John D. (travelling salesman). These same family members were listed in the Kansas City Directory in 1911 and 1914 as living together as well. Later in 1915, the two girls married. Blanche married Charles Irwin on September 1 in Parry Sound, Ontario and Annette married John Mulhaupt on October 23 in Missouri.
Caroline died in Newmarket on January 5, 1916, from a paralytic stroke. She was most likely visiting her daughter, Mildred Gilkes, as the informant on the death registration was W. C. Gilkes, Mildred’s husband. Caroline’s death registration does say she was married, which seems strange.
This particular branch of the family has not been easy to track down. It would be wonderful if some DNA matches would pop up to shed further light on them.