There were three main waves of settlement for the O'Grady family.

The first settlement was in Nepean, around Fallowfield; this area pre-existed the city of Ottawa. Honora Meara, widow of John O'Grady of Kilbarron Parish, Killaloe Diocese, near Nenagh, County of North Tipperary, Ireland arrived with her eight sons in 1826. Her husband, John, had died in 1824; their son, Patrick, also died in Ireland. This family travelled from Montreal, to Prescott, to Perth, to Nepean and Fallowfield. While living in Fallowfield, the fifth son, Thomas, and his wife, Margaret Spaine, had fourteen children, seven boys, seven girls.

Even though T.P. French, Crown Land Agent, called the second settlement in Renfrew County's Hagarty Township EMMETT, the residents and neighbours called it O'GRADY or most often The O'Grady Settlement. Even before the Ontario government opened up the Opeongo Colonization Road to settlement in the mid 1870's, free land had attracted the O'Gradys. It is likely that the oldest sons were familiar with the area from jobs on the Ottawa and Bonnechere Rivers in the square timber operations. From 1859 to 1869, the oldest sons took land grants in "an unsurveyed tract to the westward", later surveyed and named Hagarty Township. One daughter married Owen Hammill and remained on the family farm in Fallowfield. After the death of her husband, Thomas, in 1865, Margaret brought the remaining younger members to Hagarty to Lot 26, Concession 1. From here, after marriages, the family members moved to nearby lots, although the L'Orignal census of August 1862 shows the name of Thomas O'Grady on Lot 25, Concession 1, subsequently settled by his son John. Henry settled on Lot 22, Concession A. Martin, the second oldest, settled on Lot 24, Concession 1.Tom Connelly of Ottawa, a great-grandson of Martin, and his wife Shirley Mask now own the homestead built by Martin.

Each of the seven sons in turn named one of his sons Thomas after his father. As a result, the sons' names were often appended to their fathers' or spoken with the first initial of their second baptized name in order to clearly identify each in conversation: Con's Tommy, Winnie's Tom (since Henry died early in a fall from a wagon when his son was only three year's old), Rhody's Tom, Thomas L. (John's Tom), Thomas H. (Martin's Tom), Joe (Tom's Tom), Will's Tom.

The arrival of the railroad through Killaloe reduced the traffic on the Opeongo Line. The end of the pineries and lumber camps turned many settlements into ghost towns.

The third settlement followed the building of the Temiscaming and Northern Ontario Railway. This rail line opened up development in timber and farmland. In 1908 -1909, many brothers and cousins from the Hagarty settlement travelled by rail to settle on land near Englehart. One group formed what is known as "the Irish Settlement" in the townships of Robillard and Savard with Charlton as their marketing center. As a boy at Brudenell, Leo Finnerty, a barber in Kirkland Lake, remembers the exodus. He recalls standing at the roadside as the farm wagons piled with household effects and other implements rolled by on their way to the railroad station at Killaloe where the settlers belongings were loaded on cars to complete the journey to what some called the "New Ontario."

Different social conditions created the need for change. The decline in the role of the small family farm, work and business opportunities in northern Ontario and western Canada, and a recognition of the value of broader education, led the O'Gradys to scatter.