Note: This is the first article in a series which aims to describe the 230-year evolution of the Castle Frank area.
Castle Frank is a name steeped in the early beginnings of colonial Toronto. The focus is naturally on the destroyed landmark, associated with one of the city’s most important political figures. However, the area as a whole surrounding that lost site contains some of the unique topographies in Toronto and holds some of the most interesting histories and geographies the city has to offer, including hiding some of the city’s oldest roads.
Castle Frank Hill & Region
The Castle Frank region is located in the northeast corner of the Old City of Toronto of 1834. It is formerly part of the upscale Rosedale neighbourhood of Toronto, positioned in its most southeast area. Early Toronto Historian Reverend Dr. Henry Scadding, who wrote much about the topic of Castle Frank, set the following borders for the region:
“…Bounded on the east by the River Don, on the west by Parliament-street, on the north by Bloor, and on the south by Wellesley street.”Rev. Henry Scadding, The Story of Castle Frank, 1895
Geographically, the Castle Frank region forms an interesting landscape, highlighted by a table of land that narrows as it moves southeast. The hillsides leading up to this plateau are steep and cut from millions of years of history dating back to the last ice age. Together, they form some of the most pronounced topography in Toronto. At the centre of the region is Rosedale Valley, a picturesque path sandwiched between two deep ravine walls.
It must be noted that Scadding’s definition of the Castle Frank region included St. James Cemetery. While this is peculiar to think of in modern terms, the historical connection between the two landforms on either side of the ravine also might connect them geographically. Scadding also leaves out an important area north of the imaginary Bloor Street line (the street was not extended from Sherbourne Street until the 1910s), which in modern terms bear the Castle Frank name in its street names and also factor into the history of the area.
“The Gov. having determined to take a Lot of 200 acres upon the River Don for Francis, & the law obliges persons having Lots of Land to build a House upon them within a year, we went today to fix upon the spot for building his House. We went 6 miles by water & landed, climbed up an exceeding steep hill or rather a series of sugar loafed Hills & approved of the highest spot from where we looked down on the tops of large trees. There are large pine plains around it which being without underwood & can ride or walk The height of the situation will secure us from mosquitoes.”Elizabeth Simcoe, The Diary of Elizabeth Simcoe, October 29, 1794
In 1793, Upper Canada Lieutenant-Governor John Graves Simcoe granted Park Lots 1 and 2 — the area east of today’s Parliament Street to the Don River, and north of today’s Carlton Street to Bloor Street — to a Francis Simcoe. The lots were originally under different patentees, but Simcoe, in seeing the beauty of the land overlooking the river, shifted its ownership. Rather than name himself in the patent, he chose his two year old son.
To fulfill a legal requirement that patentees must build a house on their plot to retain its rights, the Simcoes selected a spot atop a narrow ridge which overlooked the Don River to the east and a deep ravine and brook to the south and west. Elizabeth Simcoe, the city’s first historian and a wonderful source of knowledge on Castle Frank and early colonial York in general, wrote:
“We walked on the Ice to the House which is building on Francis’ 200 acre Lot of land. It is called Castle Frank built on the plan of a Grecian Temple, totally out of wood the Logs squared & so grooved together that in case of decay any log may be taken out. The large Pine trees make pillars for the Porticos which are at each 16 feet high.Elizabeth Simcoe, The Diary of Elizabeth SimcoeNovember 23, 1795
The naming of Castle Frank itself came after the young Simcoe — Francis — although the usage of ‘Castle’ might be curious for some. Although the cottage was designed and built to invoke the grandeur of an ancient temple, the structure itself was likely thirty by fifty or sixty feet — not an insignificant living space for the 1790s, but not what one would call ‘a castle’ in the European conceptualizing. Rather, Reverend Dr. Henry Scadding wrote that although there was some intended humour behind it, ‘Castle’ was meant to be synonymous with the French equivalent, ‘Chateau’.
The Simcoes left York in the summer of 1796, never returning to the settlement or the chateau. Peter Russell and others used the residence for picnics and balls on occasion until 1807. During the Battle of York of 1813, it is said victorious American soldiers ventured up the Don Valley to the home, lured by the description of a castle on a map. They arrived to find a decrepit structure. By 1829, Castle Frank was abandoned, scarcely used by hunters and fishermen in the decade. Simcoe’s Chateau is said to have met its end in that year when some fisherman accidentally burned the structure to the ground.
Reverend Scadding and others visited the site of Castle Frank later in the century after its destruction. The location was seemingly marked with a depression in the land and some debris. He identified lot 8 or 9 on Castle Frank Crescent in the 1890 Goads Map as the possible location of Castle Frank. It must be noted that other maps identify the location slightly southeast of this place on the ridge, so it faces the Don River rather than Castle Frank Brook and St. James Cemetery. This seems to place it closer to lot 15 at the end of the street.
Dr. Henry Scadding showing the location of ‘Castle Frank.’, 1880.
The Road to Castle Frank
The Simcoes reached their summer retreat by canoeing up the Don in the summer (and by sled over its frozen surface in the winter) and then hiking up the hill. As for a land route, the Queen’s Rangers cleared a path north from near the Upper Canada Parliament Buildings on Front Street, an understandably frequented locale by the Lieutenant Governor. We know this route as Parliament Street today.
Parliament Street followed a relatively straight course for much of its march north. Eventually hitting an escarpment near today’s Howard Street, this is where its route split. One part moved north and west towards Yonge Street, meeting the main road near present-day Yorkville. As Yonge Street was impassable north of Lot (Queen) Street, Parliament Street was the preferred way one traveled to and from the Village of York.
The second path led east down the ridge where it followed a winding path up to Castle Frank. This was the Old Castle Frank Road.
Dr. Reverend Henry Scadding, speaking to the York Pioneer and Historical Society in February 1870, described the road as an engineering feat:
All the way from the site of the town of York to the front of this building [Castle Frank] a narrow carriage road and convenient bridle-path had been cut out by the soldiers, and carefully graded. Remains of this ancient engineering achievement are still to be traced along the base of the hill below the Necropolis and elsewhere. The brook (“Castle Frank Brook”), a little way from where it enters the Don, was spanned by a wooded bridge. Advantage being taken of a narrow ridge that opportunely had its commencing point close by the north side, the roadway here began the ascent of the adjoining height. It then ran slantingly up the hill-side along a cutting that is still to be seen. The table land at the summit finally gained by utilizing another narrow ridge. It then proceeded along the level at the top for some distance through a forest of lofty pines, until the chateau itself was reached.”The Globe, Feb 1, 1870
Reverend Scadding looks to have been referring to a path travelling east from the top of Parliament Street which ran through and along the side of the present St. James Cemetery (which may be confused with the Toronto Necropolis in the article).
The two images below look to be different views of Rosedale Valley Road as it intersects with a portion of The Old Castle Frank Road, possibly where it passed through the Cemetery (although it may also be the same path as the image depicted further down.)
The table of land in which Castle Frank was situated narrows as it moves towards its most southern and eastern point — and this seems to be where the ascend towards the cottage began.
Scadding’s description is corroborated by a later account by a ‘Historicus’ writing into The Globe:
“A road from this entrance [from Parliament and Howard Streets] passed in winding fashion down into the ravine and along the bottom of it to the east for several hundred yards, then veered to the left up a long incline made by cutting down the side of the hill to a point opposite the eastern end of St. James’s Cemetery, where it turned in a sharp curve to the top of the hill overlooking the Don Valley and thence on to Castle Frank.”The Globe, March 28, 1928
In 1871, a Colonel John Clark wrote in The Globe that he visited Castle Frank in 1829 — before its destruction — and noted “it was through a delightful road, and was in a most desirable spot for the humming mosquito”.
In 1930, an Elmes Henderson, recalling his childhood memories of the year 1849, wrote in the Ontario Historical Society Journal:
“The original cottage “Castle Frank”…remained vacant…and all that remained of it when I first saw the spot were a pile of ashes in a small depression (perhaps the cellar) and the outlines of the little garden beds in front of it, in which were some straggling remains of shrubs. There was also a bridle path to Castle Frank up the valley of the Don, traces of which still existed in my day, particularly that piece of it up the high sloping bank, and which as boys we used when going to bathe in the Don.”Elmes Henderson, “Bloor Street, Toronto, and the Village of Yorkville in 1849”, 1930
Today, the road to Castle Frank still exists in some part through the network in St. James Cemetery, in the name of a ‘Castle Frank Road’. It is unclear whether any more of the road still exists as it moves into the ravine and up the hill to the plateau. Furthermore, it is questionable whether the plateau where the chateau once stood is formerly accessible (the area is marked on parkland by the City of Toronto).
The Old Castle Frank Road to…Drumsnab?
In addition to the road to Castle Frank described above, there was a second path which travelled north from the head of Parliament Street. It curved down the steep hill until it crossed the ravine floor before ascending the equally steep ravine wall on the other side. It emerged near the modern intersection of Castle Frank Road and Mackenzie Avenue, north of Castle Frank Subway Station. This road was located north and west of the old road through the cemetery and up to Castle Frank Hill. Although the endpoint was still located on the Castle Frank plateau, this road emerged some 300 metres north of the cottage — a short distance to be sure, but further away than its southern counterpart. This road was also the ‘Old Castle Frank Road’, although it was not built as a driveway to Castle Frank itself.
In 1818, George Playter constructed a gatehouse or lodge at the corner of today’s Parliament Street and Howard Street. The house “guarded” a path which led to his land holdings to the north in today’s Rosedale where he built a residence. Playter later sold his land to Francis Cayley, who built his own home, ‘Drumsnab’ in 1834 — an estate house that still stands today. Historian Liz Lundell wrote in her book The Estates of Old Toronto that the structure at the head of Parliament Street was Cayley’s studio. The name Drumsnab meant ‘Sugar-Loaf Hill’, a nod to the raise in elevation located east of the estate.
From the gatehouse, the path did a ‘switchback’ of sorts, presumably to navigate down the profound contours of the ravine wall.
From here, the Castle Frank Road crossed Rosedale Valley. The configuration of this crossing seems unclear. The photo below from 1912 indicates a level crossing on the ravine floor, but there is evidence of an elevated bridge over Rosedale Valley Road. This bridge is named as the Parliament Street bridge over Rosedale Valley in a couple of archival image sources, so it likely was part of this same path, but its age and fate are unclear.
The road then curved up the other ravine wall and emerged near Castle Frank Avenue and McKenzie Avenue, behind 75 Castle Frank Road.
Mr. Henderson also recalled his experience with the house and the road:
“John Cayley owned the Lodge and gate at the head of Parliament Street, and the road at this date (1849) was a strictly private one leading up only to “Drumsnab” and permission to use it had to be obtained at the Lodge. This Castle Frank Road was for many years the only approach to “Drumsnab”, and when Walter McKenzie bough a large acrage near “Drumsnab” and, to his surprise, built a house and lived there in what was then thought a wilderness, his only means of access then was by this steep, winding and unlighted road passing through thick bush and crossing the little Creek by a frail bridge. Traces of this old road are still in existence.”Elmes Henderson, “Bloor Street, Toronto, and the Village of Yorkville in 1849”, 1930
Lost Rivers Toronto also mention the road also accessed John Hoskins’ estate, The Dale, as well as Walter McKenzie’s grand home, and the milkman’s cottage of Edward Nanton, who lived near today’s Nanton Avenue. They all jointly maintained the gatekeeper’s cottage.
Drumsnab and the cottage passed to the Jackson estate in the 19th century where it looks to have remained until its demolition in 1914 for the Bloor Viaduct construction. Photos of the cottage in the final years identify the Jackson standing in front of it. Famed Toronto artist Owen Staples also painted the lodge in its final year.
Although the construction of Rosedale Valley Road, the Bloor Viaduct, and Bloor-Danforth Subway have altered this Old Castle Frank Road, there are very tangible and navigable remnants of the path. There is a marked trail entrance north of Castle Frank Subway Station which forms a Discover Walk path down to Rosedale Valley Road, which is most certainly the 19th century road.
On the ascend up to Parliament Street, one passes under the Rosedale section of the viaduct. This is an unmarked, unofficial path that might still have connections to the 19th century road. One emerges at a parkette at the north east corner of Parliament and Bloor Streets, steps from where the gatehouse once stood.
Below is a Google Map created by me which overlays some historical landmarks with the modern geography: