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South Rosedale Tour

If you wish, you can print out this Tour Guide and take a walking tour of South Rosedale or visit our interactive map on the South Rosedale Ratepayers ’ Association website at www.southrosedale.org

Background History
As the eastern half of old Yorkville, Rosedale is part of one of the earliest communities in the Toronto region. The village of Yorkville, as such, began during the British Regime with the building of the Red Lion Inn in 1808. Daniel Tiers who had come in 1794 with the German Berczy Settlers - the real builders of Yonge Street - built the Inn. Tiers had run an inn for a few years in the little Town of York before purchasing a block of Farm Lot 20 in the Second Concession from the Bay from its first owner, United Empire Loyalist George Playter. Tiers' Inn was exceedingly large for its time and was built to catch traffic into the town from Davenport Road (Toronto's oldest and busiest route) and the slowly evolving Yonge Street. For many years, the Inn was a focal point of all local activity and played a role in the formation of the village and in the 1837 Rebellion. But it was a little Irishman, James Dobson, who was the first postmaster in the area and who, with other local businessmen, developed a vision of the village and brought it into being. Dobson bought a block of land almost across Yonge Street from the Inn, part of Farm Lot 21, and laid out a subdivision with some Yonge Street frontage reserved for a Town Hall. After some struggle to meet the population requirements, the Village of Yorkville was incorporated in 1853, with boundaries along Bloor from Sherbourne Street to near Bedford Road and north to the escarpment. By 1860, the Town Hall was built, a beautiful brick structure with stained glass rose windows, all designed by William Hay. Municipal services were housed in the hall and there was a farmers' market behind it until this space was taken over by the first public transportation system in the region - H. B. William' Omnibus, horse drawn vehicles which drew passengers to the St. Lawrence Market in 1866. The Village was annexed in 1883 and the Town Hall burned down in 1942. The Rosedale rose is the Rosa blanda, a sweet-scented wild rose which once grew in abundance along the escarpment. Noting this, Mary Jarvis chose the name for her house. Now rare, the rose may still be seen in Rosedale.

Beginning Your Walk
From Rosedale Subway Station go south on Yonge to Aylmer Road. On the NE corner, there once stood a blockhouse built by the government to help control the rebels of 1837. Follow Aylmer to the intersection with Severn Street, named for brewer John Severn whose huge brewery once existed to the south of the street. It drew water from Castle Frank Creek and, later, Severn Creek that meet in this area but are now buried. 25 Severn Street is the Studio Building, designed by Eden Smith and built in 1913-14 with

money supplied by painter Lawren Harris and Dr. James MacCallum. The Studio Building has become synonymous with the Group of Seven. The last great artist to work here was Harold Town. Tom Thomson's shack, now at the McMichael Gallery, was first located on Severn Creek just to the north. Go east to the intersection of Rosedale Valley Road and Park Road. Rosedale Valley Road at this point is a re - named section of Toronto's oldest road, Davenport, begun 10,000 years ago by aboriginal peoples to link the Humber and Don Rivers. The trail runs parallel to the route of Castle Frank Creek along the south side. During the French Regime, explorers, missionaries, fur traders and soldiers followed this trail and some are believed to be buried somewhere in this area.
Proceed North on Park Road past Rosedale and Avondale Roads. Park Road: Numbers 104, 108, 110 and 114 were all built between 1886 and 1889 and are on the city's Historical Inventory. Number 115 is the former home of Sir Ernest MacMillan, a founder of the Royal Conservatory of Music, composer and conductor of the Toronto Symphony and Mendelssohn Choir. Architects Page and Steele built his house in 1931.

124 Park Road, the James Boyd Davis/Geary House, is fully designated and has a heritage easement on it. Built in 1857, it has had many additions and alterations from the 1860's on. George Geary lived here from 1927 to 1958. He was Toronto’s Mayor from 1910 to 1912.
Return south past Avondale Road to Rosedale Road.
Rosedale Road is one of the oldest of Rosedale's str eets. Numbers 3, 7 and 19 were built after the turn of the century. The architect for #7 was Hugh Allward. Number 28 (1887), on the city's Inventory, was the home of James Good, builder in 1853 of Toronto's first locomotive.

23 Rosedale Road was built in 1857 as Idlewold and was later renamed Rose Cottage. Fully designated, its 1911 additions were by Alfred Boultbee and 1977 alterations by B. Napier Simpson.At 31, the original cottage called Rose Cotta ge was the home of James George Giles who owned a fine foods store on Yonge above Bloor from which he supplied railroads and sold the first Ontario grown apples. When Giles' cottage was torn down, two others on the site succeeded it. Numbers 27 (1871), 34 (1921), 39 (1891- 92) and 41-43 (1883) are all on the city's Inventory. Go back to number 30.

Rosedale House: Near 30, on the west side of Rosedale Road just south of Cluny Drive, the house called Rosedale once stood. James Small built the first part of the house in 1821. Its access road leading off Yonge above the Severn Brewery led over difficult terrain. Much of that road is now Rosedale Road. Small sold his 120 acres and house in 1824 to William Botsford Jarvis who lived in the house with his father, then brought his new wife , Mary Boyles Powell (grand -daughter of William Dummer Powell, Chief Justice) to live there in 1828. Mary named the house Rosedale and immediately began improvements. In 1835, the Jarvis's hired John George Howard to design additions and opened a new road from Yonge (now Roxborough). A fire in 1849 destroyed everything but the house. Four years later, the estate was sold to a developer who laid out new streets and 62 lots, keeping Rosedale intact on 29 acres. In 1864, the house on its acreage was bought by Sir David MacPherson of Chestnut Park to be the home of his daughter, Christina, and her new husband, Percival F. Ridout. By 1905, the house was in disrepair and was demolished when Cluny Drive was completed.

Proceed north on Cluny Drive: Number 2 (1921) is the Weldon House designed by Eden Smith, architect of many beautiful homes in the city. This home is listed as a heritage property. At 40 Cluny Drive is an attractive house that has been restored. It is worth a look. Numbers 49 (1902) and 52 (1904), located just north of Crescent Road, are also on the city's Inventory of Heritage Properties. Walk a little west before travelling east on Crescent Road.
Crescent Road: Different sections of this winding road were built at different times and had different names. The central section was first called North Drive, with the easternmost loop called Crescent Road. Look for the following houses which are all on the city's Inventory:
Numbers 35 (1895), 48 (1901), 75 (1912) the Castlemere Apartments, 84 (1899) designed by Langley and Langley, 88 (1884) with A, B and C where prominent interior decorator Budd Sugarman lives. Sugarman, more than anyone else, loves and has tried to preserve the Village of Yorkville. We continue east on Crescent Road to South Drive and walk south.

South Drive: Between this intersection and Glen Road to the east are a number of houses on the city's Inventory: Number 45 (1906) by architect Mackenzie Waters is fully designated as was number 82 (1888) which was demolished in 1978. Numbers 86 (also 1888) and 88 (1896) are listed and standing. Number 103 (1898) is an R. J. Edwards house designed for G. A Newman, while the later number116 (1905) was designed by Burke and Horwood for James Ryrie, partner in the famous jewellery firm.
Cross Glen Road continuing to follow South Drive. This section was first called Beau Street. Running east into the valley is Milkmens' Road, recalling a period in the ravine's history when, in the 1830's and 40's, there was only one cottage in the area and it belonged to a milkman. Edward Nanton bought the milkman's cottage, enlarged it and regularly enjoyed the company of drinking companions such as Sir Edmund Osler over their favoured scotch. Nanton Avenue, named

for Edward, and Hawthorne Avenues were laid out on this lot. At 160 South Drive, only the gates remain to recall one of Rosedale's most famous residents, financier Sir Edmund Osler, brother of the even more famous doctor, Sir William Osler. Sir Edmund's house was called Craigleigh and had an extensive oak forest and gardens. Osler formed the Rosedale Association in 1905 to protect the houses in the area from "progress" (i.e. city hall). This was the forerunner of the South Rosedale Ratepayers' Association. When he died, he willed his huge estate to the city which, with typical gratitude, tore down the house and converted the estate lands into public parkland. Designed by Darling and Pearson and built in 1903, the gates alone remain and are on the city's Inventory. This is an excellent place to stop for a picnic before resuming the tour.

Continue south on South Drive to Elm Avenue and turn east on Elm or return to Glen Road for the Glen Road section.

Glen Road : The present bridge was built in 1928 on the designs of city architects Woolnough, and Harris (for whom the beautiful filtration plant on the waterfront east of Victoria Park is named) and has just recently been renovated.
Turn south on Glen Road. During 1974- 75, the city placed many buildings south on Glen Road on the Inventory: 97 (1901-02), 92-94 (1900), 87- 89 (1901), 64 and 66 (1894 by architect George Martell Miller), 64 is now renovated and white-painted, 65 45 South Drive (1891), and 55 (1902 by Chadwick and Beckett).
Next we jog west, then south on Glen Road to the Morley Callaghan footbridge to cross the 55 Glen Road Rosedale Valley.

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Here we see what little protection a heritage listing offers. Developers are allowing these heritage homes to decay. On the Heritage Inventory are 14-16 (1888), 10-12 (1888 by builder A. Coleman), and 6- 8 (1883 by A. Coleman). Number 6 Elm Avenue has recently experienced a fire. On the east side of the Glen Road is 9 (1888 by Eden Smith). Numbers 1- 7 Roslyn Apartments (1911 by architect J. A. Harvey) are still attractive building after more than 90 years.
Walk back north to Elm Avenue and turn east along Elm Avenue to Mt. Pleasant Road.

Branksome Hall: To the west of Mount Pleasant and Elm Avenue is Glenhurst, one of several houses in Rosedale built by Edgar Jarvis. Glenhurst, designed by the architectural firm of Gundry & Langley was built in 1866 and had an addition designed by Smith and Gemmell added in 1880. In 1948 it was purchased and converted into Branksome Hall. The original building still exists but is hidden by the modern school addition built on its east side. Also on the Branksome Hall site west of Mount Pleasant are Denbrae, the former house of William Alexander built in 1874-76 at 3 Elm Avenue and the John Ellis House at 4 Elm Avenue.

Branksome Hall expanded to include Hollydene at 10 Elm Avenue , the home of John Blaikie, 14 Elm Avenue, the Charles Nelson House, Roslyn Apartment – Glen Road and 16 Elm Avenue , the home of Hugh Ryan built in 1879 with additions and alterations in 1898 by C. J. Gibson. All of these addresses are on the city's Inventory.

As we continue the tour going east on Elm Avenue from Mt. Pleasant, we come to 18 Elm Avenue . Both the house and fence were designed by C. J. Gibson and are on the city's Inventory. Number 20 Elm was built in 1898 by architect F. H. Herbert and has recently been beautifully restored. The Thomas Wilkins House at 24 Elm Avenue was built in 1910- 11and designed by J. Francis Brown. On the NW corner at Sherbourne, 26 Elm Avenue was built in 1914 by architect J. P. Hynes.

Numbers 44-46 (c1875), 49 (1901 by Gordon and Helliwell), 50 (1898 - the H. O'Hara House), 51 (1888 by J. A. Radford) and 53-55 (c1888 by builder J. Bedford) on Elm Avenue are all on the city's Inventory and are worth seeing.

Number 61 Elm at Glen Road was built in 1890 by J. A. Bedford who has many fine houses in the city to his credit. Number 89 Elm Avenue is the 1903 C. R. Rundle House designed by E. J. Lennox, architect of the old City Hall and Casa Loma. Number 93 Elm Avenu e, built in 1900 by architect J. W. Siddall, has a porte cochere designed by G. M. Miller for 40 Maple Avenue and moved here later. Follow Castle Frank Road. Look for 8, the Gerald Larkin House, built in 1926 by George, Moorhouse and King. Continue along Castle Frank Road to Drumsnab Road. Look east toward the end of the street.

Number 5 Drumsnab Road: Here is the oldest continuously inhabited house in the city. George Playter, first owner of the 200 acre Farm Lot 20 you have been passing through, built a lodge on this property in 1808. In 1834, Francis Cayley bought the eastern section of the Fa rm Lot containing the house, built an additional house and named it Drumsnab, in the dialect of North England for Sugar Loaf Hill in the valley adjoining the house. Sugar Loaf Hill was removed when the Prince Edward Viaduct was constructed.
Unfortunately, Playter's Lodge House was demolished in 1914, also due to the building of the viaduct. Cayley built the house from fieldstone and painted frescoes on the interior walls. The walls are 30 inche s thick. In 1850, Cayley added a second floor with bedrooms and a ballroom designed by William Thomas. Eden Smith designed further additions in 1908. From 1877 to 1965, the size of the estate was reduced but in 1967 the house was restored. Drumsnab is Rosedale's gem of gems and the pride of the city.