On this place: Riverdale Collegiate…

Slide 1 Devil's Hollow 1919
Welcome to this presentation which was given at Riverdale Collegiate on May 1, 2019.

Did you ever wonder what was here in days gone by? Who lived here? What buildings stood here? Why did they build here?

This picture shows Riverdale Collegiate on the far hill on December 22, 1919. We are looking from Prust Ave. Landfill with large concrete rubble fills the ravine in the immediate foreground. The new Hastings Avenue lies in the mid-ground and just west of it, hidden from sight, is Hastings Creek. On the slope immediately east of Leslie Street  is an orchard with an apple storage barn (cold storage).

Slide 2

Lucius O’Brien, Among the Islands of Georgian Bay, watercolour, 1886. This painting depicts Anishnaabe families similar to the Mississauga people whose traditional territory included the site of Riverdale Collegiate. The Mississauga are a group within the larger Anishnaabe (also known as Chippewa or Ojibway people).

When the first white settlers came to the area around Jones and Gerrard the Kichigo family of Mississaugas helped them adapt to life here, welcoming them and sharing food and medicine. Many native people still live in Leslieville.

For more about the Mississauga of the New Credit First Nation go to: http://www.newcreditfirstnation2015.com/community-profile/


Slide 3

Lieut. Governor John Graves Simcoe granted large parcels of land to people who supported the government of Upper Canada. Most of these did not actually settle on the land but held it as an investment, hoping to subdivide it later for sale. Riverdale Collegiate lies in Lot #11 which was granted to United Empire Loyalist Benjamin Mosely. (Mosely Street is named for him.) The writer of this article, Joanne Doucette, is herself a United Empire Loyalist being a direct descendant of Capt. Matthew Hawley of Connecticut.

For more about United Empire Loyalists go to http://www.uelac.org/

George Leslie by John McPherson Ross ca 1907
George Leslie attributed to John McPherson Ross ca 1907.

George Leslie attributed to John McPherson Ross ca 1907. George Leslie (1804-1893) was the founder of the small community that grew up around the corners of Leslie Street (named for him) and Queen Street East (then known as Kingston Road).

Leslie was a market gardener whose Toronto Nurseries became the largest tree-growing business in Canada in the 19th century. He was a public school trustee and a strong advocate for free education for everyone. His market garden was between Queen Street and Ashbridge’s Bay (south of Eastern Avenue) and Leslie Street and Caroline Avenue (named after his first wife Caroline Davis).

His home was at the northeast corner of Queen and Jones and Leslie Grove Park is the northern part of his arboretum and site of his greenhouses.

Below 1868 Gehle, Fawkes & Hassard: Reconnaissance Sketches of Toronto Area.

Slide 4b

This map was prepared by British army officers in order to secure Toronto in case the Fenians attacked the city. The curved line across the map is what is now the GO Train line (CNR) but was then the Grand Trunk Railway line, the first rail connection between Montreal and Toronto.

The note “brickfield” is just west of what is now Jones Avenue. Gerrard Street doesn’t exist yet but a faint line of dashes just below “Nursery Grounds” on the right of the map marks where the street will be in the future. The school marked on the map is the Leslie Street school still on that location today. The north-south street west of Jones is Pape Avenue and to the west of that is Logan Avenue. Mill Road is now Broadview Avenue. It was originally an indigenous trail.

The creek immediately to the east of Riverdale College (forked creek on the map) was Hastings Creek flowing through the Nathaniel Hastings farm. The other creek on the map was Leslie Creek and it began in springs just south of Danforth Avenue. Both creeks entered Ashbridge’s Bay where the Loblaws parking lot is at Eastern Avenue and Leslie Street.

Rembler Paul (1832-1916) was George Leslie’s brother-in-law, married to Elizabeth Davis (1831-1914). Rembler Paul was an English veterinarian, horse dealer and real estate agent. Gerrard Street East was originally called “Rembler’s Way” or “Rambler’s Way” after Rembler Paul. 

Slide 5b
Elizabeth Davis

George Leslie’s first wife, Caroline Davis (1820-1852), and her sister were the daughters of one of Toronto’s first police officers. (Both loved animals and are buried in a tomb on a mountain top in British Columbia along with the family cat.) 

for more about Rembler Paul and Elizabeth Davis:


Slide 5a
Rembler Paul

Leslieville showing Gerrard Street East (Late Ramblers Rd.) at top of map. Detail from Goads Atlas 1890 Plate 47

Property owners from the first settlers to the Toronto Board of Education.

Source: Book 489 Block 5 Lot 11 Concession 1

The first settlers on the site of Riverdale Collegiate — from Benjamin Mosely to James M Strachan (real estate agent)

From 1854 to 1890

1898 to the Board of Education, purchased for Riverdale High School

40 of Book 489 Block 5 Lot 11 Concession 1
Samuel Gerrard (1767-1857) was a fur trader, business man, financier and the second president of the Bank of Montreal. Gerrard Street was named for him.


For more about Samuel Gerrard go to: http://www.biographi.ca/en/bio/gerrard_samuel_8E.html

Jones Avenue was first called Clifford Street after a well-known local family. It was renamed after John Jones (1843-1918) who was born in Glamorganshire, Wales, and became a sailor, coming to Canada in 1850. While he eventually became a city alderman, and Works Commissioner, he was a jack-of-all-trades: market gardener, brickmaker, real estate developer, community activist and He was lodge master of Leslieville’s L.O.L. No. 215 for seven years. L.O.L. means “Loyal Orange Lodge”.


For more about John Jones see

Four of these photographs are from the Globe, September 18, 1909  and show the area as it developed in the latter half of the 19th century. The three main industries were market gardening and small farms (hay stacks upper left), livestock (man driving cow lower left), and brick making, as well as sand and gravel extraction lower right). That is why I named my history of the area: Leslieville: Pigs, Flowers and Bricks. Sheep are grazing at the northeast corner of Greenwood and Gerrard in the photo top right!

To read or download free of charge my book, Leslieville: Pigs, Flowers and Bricks go to:

However, the gentleman with the beard in the lower middle photo was an unusual and intriguing member of Leslieville’s rural industrial economy.

Joseph Simpson (c. 1825-1898), a Jewish American immigrant, began a successful woolen mill in Leslieville, buying up large expanses of land to graze sheep. He was originally from South Carolina and had joined the 1849 gold rush to California where he made his fortune not digging gold, but selling underwear to the miners. 

Unwilling to fight in the Civil War, he came north to Leslieville and began a knitting mill at Coxwell and Queen. In 1872 he moved downtown and built a new knitting mill, now Berkeley Castle, at Berkeley and Front Streets, to produce high quality woolen underwear.

He grazed his sheep under the trees in Leslieville’s orchards including those where Riverdale Collegiate is today. Sheep acted as effective lawn mowers, cutting the grass short, fertilizing the soil, and removing the undergrowth that housed and sheltered the pests that attack apples. His fine merino sheep grew fat and happy while the apples grew large and shiny and orchard owners and wool merchant made money.

Joseph Simpson was one of the founders of the Canadian Manufacturers’ Association.

Mr. Joseph Simpson was always an active member of the Jewish community, especially in its younger days, and throughout his life subscribed liberally to all Jewish charities. He also took a keen interest in civic and municipal affairs & never hesitated to combat any measures which he believed not thoroughly intended for the welfare and prosperity of the city of his adoption. He was often pressed by his numerous friends to enter public life, but he never consented. He was a very prominent and active member of the National Club, R.C.Y.C. shareholder, and member of the Athletic Club, and at the time of his death was one of the oldest members of the Board of Trade.”

“The Outstanding Personalities of Toronto Jewry During the 19th Century” From The Jewish Times, 1912 (as reprinted in The Jewish Standard, 1934) by S. J. Birnbaum

Sheep, small flock on hillside, November 8, 1926.

Ad, Apples, Apples, Apples from the Toronto World, October 12, 1885. An apple storage shed, 1908. A listing of some of the many varieties of apples available in the 19th century (from Toronto Nurseries catalogue)

A nineteenth century illustration of a now rare variety of apple, “Seek No Further”. US Dept of Agriculture Pomological Watercolor Collection Rare and Special Collections, National Agricultural Library A man picking apples, Ontario.

The 1840’s were a golden age of greenhouses. For the first time, technology was available to make large sheets of plate glass and iron frames. Steam engines heated these “crystal palace”. The greenhouses and their crops amazed people. For the first time, fruits and vegetables became available and affordable for the middle classes year round.

In 1851 the great glass structure, the Crystal Palace, designed by Joseph Paxton as the centerpiece of the first Great Exhibition, was opened. Paxton was knighted for his efforts. This is Toronto’s very own Crystal Palace (Crystal Palace, 1871. Exhibition Place & CNE Archives).

Market gardeners near to Jones and Gerrard, 1890 City of Toronto Directory. For more about Timothy Lynch (highlighted in orange) read on!

To be continued…

Published by Leslieville Historical Society

Welcome to the Leslieville Historical Society's website. Please feel free to join us, to ask questions, to attend walking tours and other events, and to celebrate Leslieville's past while creating our future. Guy Anderson, President, Leslieville Historical Society and Joanne Doucette, local historian and webmaster.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: