Annie McKinnon was born at Point Deroche, PEI to Angus James McKinnon and Agnes MacInnis. Her parents came from Lot 47 PEI. In 1881, she married James Doyle in Mount Stewart, PEI and moved to America in 1886 with her first two children, Joseph and Christina.

Her husband had taken a job with the Fitchburg Railroad Company and they lived at 55 Maverick Street in East Boston, just a block away from the Most Holy Redeemer Church. She had a third son Walter Doyle in East Boston in 1887, a year after they moved.

In August 1889, her husband James was killed in a rail-yard accident leaving her a widow with three toddlers.

In 1891, she remarried to William J. Wilkie, a ferry and tug operator in East Boston, who lived and worked close by. She had 8 Wilkie children with him and the Doyle children from her first marriage were raised together in various places they lived: 35 New St and 373 Border St in East Boston, as well as at 5 Wesley St (now Emmons St) when Wilkie was working as a Boston Harbormaster.

By 1920, most of her kids had married off. The Wilkie girls married to Rich, Clark and Curran husbands and moved to Chelsea where they ended up having large families. Joseph F. Doyle had moved to Dedham, MA by then. Christina Doyle's husband had died in 1916 - the three children scattered to Kelly relatives and briefly with Annie Wilkie. Christina Doyle eventually re-married to a Walsh and also moved to Chelsea around 1923.

Annie died in 1920. She was buried at Holy Cross Cemetery under the name Annie Wilkie in Malden at the grave plot she bought for her first husband, James Doyle. Buried with her are her daughter, Annie Loretta Wilkie, who died a few months later, her son Walter Doyle and his wife Louise.

William J. Wilkie remarried again in 1932 to an older lady in Revere but then died a few months later. He is not buried with Annie but rather in his second wife's family plot in Holy Cross.

In total, Annie McKinnon had 29 grandchildren - most living in Chelsea and further, 90 great-grandchildren.