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{Chapter Seventeen}

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From the Macaulays to James Dean

This farmland had it all — a judge, a mansion, an innkeeper, a doctor, a reverend, a reverend-doctor, a succession of farmers, and even its own James Dean. Today, it is pleasant, leafy, and residential. Lot 25-2E was always beautiful, bordered on its western edge by the same stretch of the East Don River that runs through Mazo de la Roche’s Windrush Hill and on its eastern border by the German Mills Creek. It stretched along the south side of Steeles Avenue from Bayview Avenue to Leslie Street. Like most of this part of North York, it was beautiful, rolling land with deep river valleys and fresh forested vistas around every turn. Farmhouses and farmland survived here until 1972. Today, although all that is left are stories and photographs, it is still quite possible to conjure up a feeling of what must have been.

It was most unusual for the Crown to grant farm lots to women in the eighteenth century, but there weren’t many women like Elizabeth Macaulay. A childhood friend of Elizabeth Simcoe — the wife of Upper Canada’s first lieutenant governor, John Graves Simcoe — the former Elizabeth Hayter had married Dr. James Macaulay in 1790, after he had served as a surgeon in Simcoe’s regiment during the American Revolutionary War. In 1791, the two families travelled together from Britain to Upper Canada and settled in Newark, today’s Niagara-on-the-Lake. In 1792, the lieutenant governor decided to move the capital of Upper Canada to York.

The Macaulays accompanied the Simcoes once again, and, when they arrived in York, Dr. Macaulay was charged with creating the new town’s first hospital and medical board. He also asked for, and was granted, an astonishing amount of Crown land, including 1,600 acres for himself, 1,200 acres for Elizabeth, and 660 acres for each of the couple’s children. Part of the land granted to Elizabeth was the two-hundred-acre Lot 25-2E on Steeles Avenue.

The family’s first home, named Teraulay Cottage after a combination of James’s and Elizabeth’s family names, was located in the town of York, on the site where the Holy Trinity Church would later be constructed. Other family members also built homes nearby, and soon the area running from Yonge Street to Osgoode Hall was known as Macaulaytown — the first suburb in Toronto. James and Elizabeth witnessed the dawn of a whole new society, yet they could never have imagined what the little cluster of log cabins that was once the town of York has exploded into today. Macaulaytown is now covered by the Eaton Centre, Old City Hall, New City Hall, office buildings, and hotels. After Elizabeth died in 1809, James would marry Rachel Crookshank, another Loyalist and close friend of Elizabeth Simcoe. Rachel’s brother, George Crookshank, is featured in the chapter on Lot 24-1E. Dr. Macaulay retired to York in 1817, after spending twelve years in Quebec overseeing hospital construction and serving as medical examiner. He died in 1822.

The Macaulay children capitalized on the head start that their parents had offered them and built on the family’s accomplishments in most impressive ways. Youngest son Allan was the first missionary to be put in charge of St. John’s Anglican Church in York Mills. Born in 1804, he was still a young student studying under Dr. John Strachan, then Archdeacon of York, when he was ordained as Reverend Allan Macaulay on October 28, 1827. His primary duty was to establish regular Sunday services at St. John’s, the second church to be built in this part of Upper Canada after the initial log St. James’ on King Street, which opened in 1807. He was also part of the consecration of the second limestone St. James’ on September 2, 1828. Tragically, Allan was plagued by ill health of an unrecorded nature, which, despite his bravest efforts, sometimes prevented him from conducting the Sunday services at St. John’s. On those Sundays he would still try to drag himself out of his sick bed to at least attend the services, even if he was too ill to perform them. He died in 1830 at the age of twenty-six.

The Macaulay sons were all educated at Dr. Strachan’s schools in Cornwall and York, and although not all of them entered the clergy as Allan did, his brother William would leave a religious legacy in one small Ontario town that resonates to this day.

Shortly after William Macaulay was ordained, he moved to Picton, where he founded the local Anglican congregation and became the community’s early spiritual leader. Prince Edward County was a favourite with United Empire Loyalists at the time, and William, as the son of a prominent Loyalist, had been granted much of the land that now comprises the town of Picton when he was just nine years old. Though well-born, he was generous to a fault, donating land for two churches and the courthouse, as well as personally surveying the new streets that were laid out in the town. Actually, he really wasn’t much of a businessman, and, though he also worked as a miller and operated a wharf back when Prince Edward County was a major shipping centre, his lack of killer instinct soon landed him in financial difficulty. He was known to sell his land below market value when he was dealing with a deserving farmer who was short of cash. He also allowed tenant farmers on his land to fall far behind in their rent, as he had great faith in his fellow man and believed that, ultimately, all would turn out well. The construction of his own rectory brought him to the edge of bankruptcy and resulted in his older brother, John Simcoe Macaulay, being given his financial power of attorney. William was now free to concentrate on his ministry, knowing that his other affairs were in capable hands.

The rectory, when completed around 1839, was considered the finest house in the county. The red-brick, neo classical-style home was perfectly proportioned and beautifully detailed. Featuring every modern convenience of the day, it was situated next to the newly constructed St. Mary Magdalene Anglican Church. William was also the chaplain to the Legislative Assembly of Upper Canada for a time, but it was his work in Picton, where he lived out the rest of his life while serving as rector from 1827 to 1874, that would define his legacy and leave us with one of the only traces of the Macaulay family to still physically exist. Today, after thousands of volunteered hours, the rectory has been meticulously restored to its mid-nineteenth-century perfection. This breathtakingly beautiful restoration is well worth a visit. The Anglican church, now a museum, is just next door.

John Simcoe Macaulay, the eldest brother, who took over William’s finances, was a colonel in the Queen’s Rangers before serving on the Legislative Council of Upper Canada from 1839 to 1841. He was also a magistrate, postmaster, surveyor general, inspector general, and an agent of the Bank of Upper Canada in Kingston. He retired to England in 1843, where he died in 1855 in his sixty-fourth year. The final son, James Macaulay, was arguably the most impressive of all.

James was born in 1793, two years after John and one year before William. He was drawn to the legal profession where he was called to the bar in 1822. He worked extremely hard and was appointed as a judge in 1829, the same year he assumed ownership of Lot 25-2E. He served as chief justice from 1849 to 1856, and was knighted just before he died in 1859. At the time of his death, he had assembled the most impressive title of Chief Justice, the Honourable Sir James Buchanan Macaulay, and yet he was also remembered for his commitment to helping the less fortunate.

Ten years after Sir James’s death, his widow sold their home, near the southwest corner of Yonge and College Streets, to the Bishop Strachan School, which remained there for forty-five years until the school moved to its present campus on Lonsdale Road. The Macaulays’ former home sat vacant for a while before being demolished for the construction of the T. Eaton Company Limited’s College Street store that opened in 1930. Sir James’s daughter, Elizabeth, continued the family’s involvement with the Anglican Church when she married the “right-irascible” Reverend Doctor Richard Mitchele.

Richard Mitchele was a graduate of Trinity College in Dublin. His first posting in Upper Canada was to Holy Trinity Church, which stood on land that the Macaulays had donated to the church when they vacated their first home in Upper Canada. When he first arrived in York he was simply the Reverend Mr. Richard Mitchele. It wouldn’t be until 1859, after he received his LL.D. degree from Trinity College in Dublin, that he became the Reverend Doctor Mitchele. He was posted to St. John’s after his stint at Holy Trinity, and arrived in York Mills in July of 1852 with a fervent desire to set the records straight — literally.

It seems that certain parts of the original church register had been filled up by 1849, six years after the construction of the current brick church. A new register had been obtained for recording marriages, baptisms, and burials, while vestry minutes continued to be recorded in the old registry. In addition, the church wardens at St. John’s had started a new book to keep track of financial records beginning in 1851, though, curiously, previous financial records remain unaccounted for to this day. It comes as no surprise then that the new reverend was less than pleased with his introduction to the new parish, since the church places great importance in proper record-keeping. He did not deliver his verbal report on the state of affairs at St. John’s until 1854, and, when he did, it was tinged with his annoyance at the missing records. Nonetheless, it was he who consecrated the church on October 18, 1854.

Dr. Mitchele helped improve the church’s finances, but a financial depression in 1857 burdened little settlements like York Mills until early in the 1860s. Before the congregation of St. John’s had fully recovered from the depression, Dr. Mitchele left on an extended trip to England in 1861. This was to be the first of several unexplained absences that were born with mild annoyance by the congregation as they welcomed a series of temporary clergy. It was during this first absence that nineteen-year-old John Squire was hired as sexton of St. John’s, a position he held until his death in 1931. Dr. Mitchele returned in the summer of 1862, only to disappear again in the summer of 1863.


This elegant Georgian home graced Lot 25-2E near Bayview and Steeles until 1972. Built by William Dickson over one hundred years earlier, the house was photographed by Lorna Gardner in 1962.

Courtesy of North York Historical Society, NYHS 319.

Dr. Mitchele reappeared at St. John’s, quite unexpectedly, in August of 1864. In September, he called a vestry meeting where he himself recorded the minutes in a strong, angry hand and used the same violent pen strokes to slash the word “cancelled” across the minutes of all meetings that had been held in his absence. Two months later he returned to England and never came back, while St. John’s remains a cornerstone of the community to this day.

The Macaulays’ involvement with Lot 25-2E had ended many years earlier when, in 1832, Sir James B. Macaulay sold the south half of the lot to William Dickson, who had lived in North York for over thirty years, and the north half of the lot to Joseph Abraham (also spelled Abrahams in some records), proprietor of the Green Bush Inn at Yonge and Steeles in 1833. Downtown Toronto remembered the Macaulays with a series of streets that were named after the family, including Elizabeth, Terauly, Macaulay, Louisa, Hayter, and James Streets.

William Dickson bought the one hundred acre southern half of Lot 25-2E for slightly less than £150, a relatively small amount for North York farmland at the time, and likely indicative of the fact that the property had probably not been cleared or built upon. This seems reasonable since the Macaulays were quite busy indeed with their pursuits in town. Well-connected Loyalists like the Macaulays were often granted title to their land even if they never lifted a finger to fulfill the conditions that other settlers had to complete before the Crown would hand over the deed. This practice resulted in many uncleared road allowances, further impeding the already difficult travel of the early settlers, and becoming one of many ongoing grievances that would eventually lead to the Upper Canada Rebellion of 1837. But back to William Dickson.

It would be interesting to report that this is the same William Dickson who emigrated from Scotland to Lower Canada in 1785, built the first brick house in Upper Canada after settling in Niagara in 1792, killed William Weekes, a member of the House of Assembly, in a duel in 1806, bought 95,000 acres of former Six Nations land for £15,000, where he built the town of Galt, and served on the Legislative Council of Upper Canada, but that is not the case. It seems that there were several prominent William Dicksons in Upper Canada at the time, and this Dickson was one of the other ones. Fortunately, he also knew how to build a brick house.

The photo of Dickson’s home shows evidence of several later additions, including the enclosed vestibule, and wings on either side of the main structure. The six-over-six-pane sash windows are likely a later and much easier to clean version of the twelve-over-twelve pattern common to Georgian houses of the mid-nineteenth century. (As roads became smoother, it became easier to transport larger pieces of glass). William Dickson was by no means a newcomer to North York, having bought Lot 16-1W from the original grantee, James Johnson, in 1798. He sold the lot to Joseph Shepard in 1802, where, thirty-three years later, Joseph would build the house that stands to this day at 90 Burndale Avenue.

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