Lots of places to start, but it seemed logical to start with the owners of the house. I hit the census records looking for Oliver W. and Mary J. Barnard around the turn of the century. A likely match popped up at the top of the results list: Oliver and Mary J. Barnard, living in 1900 in Manteno, Kankakee County, Illinois.
It did not take me long, digging into the various public family trees on Ancestry, to confirm that this was indeed the correct family. As I continued to check census records and family trees and do a lot of Google searches, I was able to place each one of the women and even the unnamed baby.
Oliver W. Barmard was an early settler of the Manteno area, receiving a land patent in 1866 for 160 acres in Kankakee County, Illinois. Oliver was born in 1828 in Wayne County, Indiana, to parents William and Sally (Williams) Barnard. By 1850 he had migrated from the mid-eastern border of Indiana to LaPorte County, Indiana, just south of Lake Michigan. He receives his land patent in 1866 and by the 1870 census he has settled in Kankakee County, Illinois. In May of 1877 he makes an appearance in Chicago for his marriage to Mary Jane Williams. They would have four children, two girls and two boys, all born and raised in the Manteno area. He died on August 14, 1907.
I theorized at this point that this photo was taken in 1907 and that Oliver was the "Grandpa" who died that summer. As I progressed with identification of each of the persons in the photo, the theory held and I believe that this was indeed a photo taken about the time that Oliver died.
Mrs. Mary J. Barnard herself is in this photo, the woman seated in the middle holding "Clarence Dole's baby".
Two of the ladies in this photo are daughters of Oliver and Mary Barnard. The woman standing on the left in a dark dress is identified as Mrs. F. Loretta (Barnard) Baird. Daughter Francena Loretta was born in 1851 and would have been 56 in 1907. She married in 1872 to Alexander Baird and the couple had five daughters and two sons.
The woman seated at far right is identified as Mrs. Izetta (Barnard) Dole-Townsend, the other daughter of Oliver and Mary. She took a little work to run down, because it turns out that she went by her middle name Izetta rather than her given name of Amelia. I spent a little time trying to tie her to the other woman with the Dole surname, thinking they might be sisters-in-law and erroneously looking for a brother of the named Clarence Dole as Izetta's possible husband. It wasn't a bad idea, but it sent me down a rabbit trail I should have avoided.
Because it turns out that Amelia Izetta Barnard married twice and produced children with both husbands, quite a number of years apart. Izetta was born in 1862, and would have been 45 at the time of this photo. She married first in 1883 to Ira Burton Dole, a salesman, with whom she had three children: Lillian, Clarence Arthur and Ira.
Son Clarence married in 1906 to Olive Mabel Viall, so the woman standing on the right and identified as Mabel (Viall) Dole is Izetta's daughter-in-law. That makes the baby held by Mary Jane Barnard her great-grandchild and Izetta's grandchild. A quick check of the 1910 census identified that baby as Edwin B. Dole, who was born in 1907.
Izetta's husband Ira died at the early age of 28 in 1888. In 1900 Izetta and her children are living with her parents. In 1902, Izetta remarried to William Townsend, a store merchant in Manteno. The couple had two daughters, Lela, born 1904, and Marian Ella, born 1906. These are the two little girls in the foreground of the group. They are also the aunts of the baby.
That leaves one lady left to identify. The woman seated on the far left, identified as Polly (Barnard) Maulsby, proved to be the sister of Oliver Barnard. She herself would pass away in the next year.
A couple of mildly interesting tidbits surfaced during my research of this family. Son/husband/grandchild Clarence Arthur Dole turned out to be quite the little gadabout. Clarence was born in Chicago, married Mabel in Kankakee in 1906, was living in Nebraska in 1910, in Colorado in 1920 (where we learned that little Edwin acquired a younger sister Marjorie), married a second time in 1927 in Yuma, Arizona, was in Wyoming in 1930 and died in 1958 in California. No grass growing under that boy's feet.
The other interesting tidbit concerns Grandpa Oliver Barnard. He is mentioned in many a Google search result as being a source of an early spelling of Manteno as Manteneau. References are made to some books he wrote, including local histories of the Manteno area. A final search of online books yielded a volume of poetry, Poems of Hope, which was published in 1906. The little book includes a photo of Oliver and among the many poems are "To Izetta on Her Sixteenth Birthday", "Our Two Boys", two poems addressed to his father and "Lines Addressed to Miss Lillian Dole". I think he must have been a loving son, father and grandfather to write these tributes.
What fun to puzzle out all these familial connections.