City of Toronto Honours Ann O’Reilly

Ann O’Reilly was a great woman.

The need to achieve greatness and strength and perseverance was thrust upon her. She did not seek it out.

Records show that Ann was a native of Ireland who immigrated to the then wilderness of Upper Canada in 1827 when she was only two or three years old.

Not much is yet known about Ann’s early and formative years growing up in Upper Canada other than knowing her father had a farm, located some distance north-east of the town of York (now Toronto).

No marriage record has yet been found but likely sometime in the early 1850’s Ann married another Irish immigrant named Patrick O’Sullivan. Around 1860, the two opened a two bedroom hotel and eatery on a piece of the farm owned by Ann’s father. The location of the hotel was the north-west corner of what is known today as the intersection of Victoria Park Avenue and Sheppard Avenue East.

The records also show that Patrick and Ann had three children: Ellen, born about 1854; Thomas, born about 1856; and, finally Michael, born in 1858.

Just one year after opening their hotel, Patrick died. Ann was faced with grieving the loss of her husband, the operation of the hotel, and three young children to raise, the eldest of whom was only about 6 years of age.

Ann demonstrated a fortitude, resolution and strength of character we would all hope is within us. She kept the business of the hotel going and she raised her children through those tough times. A single mother and business owner in the second half of the nineteenth century was not common.

Eventually, Ann would turn over the running of the hotel to her youngest son Michael, the husband of my great grandmother’s sister Ellen Fitzgerald. But not without staying on, no doubt to continue to work and provide guidance.

The hotel became of fixture in its part of York Township, eventually part of the borough,┬áthen city of North York and, finally city of Toronto. Michael opened a post office in the hotel and the area became known as O’Sullivan’s Corners, a moniker that remained at least well into the 1950’s.

On June 19, 2015, the City of Toronto recognized the pioneering contributions of Ann O’Reilly by naming a street after her.


Ann O'Reilly Road, Toronto, Ontario, Canada

Ann O’Reilly Road, Toronto, Ontario, Canada

A new street named Ann O’Reilly Road was unveiled. City of Toronto Councillor Shelley Carroll was on hand to do the honours along with Ann O’Reilly’s descendants. Ann’s great-great grandchildren Margaret O’Sullivan, Dennis O’Sullivan, and Darlene Hall, my previously unknown third cousins, all helped unveil the new street sign.

Descendants of Ann O'Reilly unveil the new Ann O'Reilly Road street sign, June 19, 2015

City Councillor Shelley Carroll and Descendants of Ann O’Reilly unveil the new Ann O’Reilly Road street sign, June 19, 2015

As a footnote, I was invited to this special occasion due to the diligent work of Mary Ann Cross, a member of the North York Community Preservation Panel and champion for the naming of streets and parks in North York to honour its early settlers. Community preservation panels act as advocates for on heritage issues in their community. Members of these panels are appointed by the Toronto City Council.

Mary Ann saw my connection to the O’Sullivan family and Ann O’Reilly while reviewing my online Ancestry family tree. Without that online tree, I might never have known about the street naming, let alone have been invited to attend and participate in the street sign unveiling. Oh, and I probably might never have had the chance to meet my O’Sullivan cousins.

Another good reason to have an online family tree!