The Montreal that Cairine came to know between 1890 and 1909, when she married and went to live in Rockland, Ontario, was only a fraction of the city — indeed, only a portion of the district inhabited by English-speaking Montrealers, who, for the most part, lived west of St. Lawrence Boulevard. Geographically it encompassed the area bounded by University Street to the east, Guy Street and Côtedes Neiges to the west, Dorchester Street to the south and Cedar and Pine Avenues to the north. Here, in what would later be labelled “the Square Mile,” flourished an English-speaking society that boasted some of Canada’s wealthiest tycoons, many of them self-made men, who, for the first time in their lives, had money to squander. And, in imitation of the great fur trading barons at the end of the eighteenth century and the beginning of the nineteenth, many of them did.
The streets of the Square Mile were filled with the residences of magnates: Sir Hugh Allan (shipping), Lord Strathcona (CPR), Lord Mount Stephen (CPR), Lord Atholstan (Montreal Star), Sir William Collis Meredith (law and banking), Sir William Van Home (CPR), Sir William Macdonald (tobacco), Greenshields (law, wholesale dry goods and stockbroking), Dawes (brewing), Birks (jewellery), Morgan (department store), Ogilvie (flour), and Molson (brewing), to name but a few.28 But although every street in the Square Mile was considered fashionable (and in actual fact some of the most impressive homes, those belonging to Lords Strathcona and Shaughnessy, were located on Dorchester west of Guy) not one was more fashionable than the mile-length section of Sherbrooke Street that ran between University and Guy.
An elegant residential stretch, rivalled only by Dorchester Street, it abounded in mansions built of handsome limestone obtained from local quarries. The architecture of these varied greatly, some being formal and rather austere like Kildonan, others Scotch baronial like the “grandly artistic house” built by Sir George Drummond at the southeast corner of Sherbrooke and Metcalfe Streets. No matter what its architecture, though, every house invariably had three dining rooms: the main dining room, the children’s, and the servants’ hall. There was also a formal drawing room and a spacious conservatory, often supported by a large greenhouse which grew not only an abundance of flowers, but sometimes fruits, such as nectarines, grapes and peaches.29 Most households had a staff comprising a coachman, groom, chauffeur (after the advent of the automobile), butler, cook, kitchen maid, housemaid, tablemaid and a permanent charwoman. A few establishments had many more than nine servants.
Sherbrooke Street was the aristocratic street of Montreal before commercialization began to make itself felt in the late 1920s. Indeed, this artery of success created such an awesome impression on late Victorian observers that the authors of an article on Montreal in 1882 stated emphatically, “Sherbrooke Street is scarcely surpassed by the Fifth Avenue of New York in the magnificence of its buildings.”30
Four or five blocks east of Kildonan, on Sherbrooke Street, was one of these magnificent edifices, the massive stone residence of Sir William Van Home, a friend and business associate of Cairine’s father. In this impressive, 52-room home could be found one of the largest collections of Japanese porcelain in North America as well as a mammoth art collection, both assembled with the same spirit and energy that this huge Renaissance man had brought to the laying of the Canadian Pacific Railway’s tracks when he was in charge of the railway’s construction.
Across from the Van Home mansion, on the south side of the street, just west of Peel, at number 916, was the “young ladies’ school” where Cairine Mackay obtained her early education, for, unlike children from many other wealthy families, she was not educated by a governess and tutor at home. Known by the delightfully old world name of “Misses Symmers and Smith’s,” it frequently enjoined its pupils — who were always referred to as “young ladies” — to cultivate that most desirable of attributes, the soft, low voice of woman. It also appears that Miss Smith was fond of quoting the verse in Ecclesiastes that reads, “Whatsoever thy hand findeth to do, do it with thy might.” This, at any rate, was the injunction that above all others made a deep impression on Cairine Mackay because in later life whenever she was tempted to skimp on a job, she would recall these words and then strive to do her best.31
Her final school years, 1899-1902, were spent at Trafalgar Institute, which opened in 1887 in a red sandstone house on Upper Simpson Street, just a short walk from Kildonan. At this most exclusive of ladies’ finishing schools, Cairine Mackay was deeply influenced by the headmistress, Grace Fairley, a remarkable woman, who demonstrated by word and deed her firmly held conviction that “It is much better to sacrifice all in defence of country or ideals, even though one knows at the outset that there is no hope, than it is to take the easy way out.”32 This maxim, like the verse from Ecclesiastes, made a lasting impression on Cairine Mackay and became an infallible guide in the years that lay ahead.
Her firmly held principles, notwithstanding, Miss Fairley does not fit our stereotyped image of the Victorian headmistress. Far from being intimidating, she was an approachable person who stood at the head of the school stairs and personally welcomed each pupil at the start of the school day. She also expressed a great love of flowers, children and small animals and tried to inculcate in her students an understanding and appreciation of each season and its particular beauties. Moreover, where another teacher might insist on adhering to a rigid timetable and a prescribed format, this gifted classics scholar was not above encouraging her pupils to close their books and to air their thoughts on topics quite removed from the lesson at hand.
Such is the stuff of which fond school memories are made, at least for Cairine Wilson, who thirty years after graduating from her alma mater, recorded them in a tribute to Grace Fairley, who had died a few months earlier.33 Still later, beginning in the 1950s, and continuing until her death, the Senator donated a special award, named the Fairley Prize, to a member of the graduating class at Trafalgar who had made an outstanding contribution to school life. Since Cairine Wilson’s death the prize has been donated annually by the Trafalgar Old Girls’ Association “ in memory of Miss Fairley and the Hon. Senator Cairine Wilson.”34
Cairine enjoyed studying, her favourite subjects being history and mathematics. No doubt to the delight of her education-conscious father, she earned good marks, ranking second in Form IV, third in Form V and first in her graduation year, by which time the school body had grown to seventy-eight boarders and day pupils and a separate day school wing had been added to the original house.35 At Trafalgar she learned French, which would prove an invaluable asset in later years, and developed close friendships with Elsie Macfarlane McDougall, Louise Hays Grier, Winnifred Stanley Hampson and Pauline Hanson Davidson. No matter what the years would bring in the way of vicissitudes and changing circumstances, they would remain “best friends,” corresponding, telephoning each other, and exchanging gifts at Christmas and on birthdays. And when it came time to draw up her will, Cairine Wilson would remember Elsie McDougall’s children just as if they were members of her own family.36
However, although she was a good student and would probably have benefited a great deal from a university education, Cairine Mackay never went on to higher learning. Probably she, like most other women raised in the Anglo-Celtic tradition, regarded the life of the mind as essentially a male preserve. McGill could take the bold step of admitting women for the first time in 1884, but in Cairine Mackay’s circle in 1902, it was still unthinkable for a woman to enrol in a university program — unthinkable, that is, for everybody but precocious Marion Creelman Savage. Born in Toronto, she studied at the prestigious American women’s college, Bryn Mawr, Queen’s College, London, and McGill University, from which she obtained a bachelor of arts degree in 1908. It was probably while she was enrolled at McGill that she came to know Cairine Mackay who became a lifelong friend.
Although school and church were important influences in Cairine Mackay’s life, social functions and sports were not neglected.