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WHS promotes respect for community roots, artefacts, and heritage structures through advocacy, education, and community connections.
Weston, Ontario, Canada Last update: December 20, 2025
Weston Historical Society Window Collage
1. Weston Ice Company
Before refrigerators and electricity, people kept food cold in ice chests that contained large blocks of ice. Weston Ice Company would deliver the blocks whenever needed. The ice was probably taken from the Humber during the winter and then kept solid in large warehouses full of straw.
2. Kenjockety
Now known as 140 Church Street, this house was built around 1901 and purchased by the Coon family in 1902. Hervey Coon was a Weston Councillor for 1904 and 1907. He was on the Weston Board of Education, and he was a member of the Methodist Church, the Red Cross Society, and the Weston Horticultural Society. The Coon family gave the house its name.
3. The Allen Family
All three sons went to fight in WWI, but only one came home. Jack Allen's two younger brothers, Robert and Leonard paid the supreme sacrifice – Robert in 1918 and Leonard in 1915. Then the father, Robert J. Allen, died on July 7, 1918, before Jack got home. At the time, there was a suggestion that Maria Street (Queens Drive) should be changed to Allen Avenue.
4. War Loans
Later on called Victory Loans, war loans were Canadian government appeals for money to finance the war effort in WWI and WWII. This second effort came out in 1941, and there would be more. Weston met its quota every time.
5. Irvine Blacksmith
At the corner of John and Main (Weston Road) Streets, the sign, "Weston Shoeing Forge, Irvine Shoer, General Blacksmith Shop" was prominently displayed. James Irvine was born in Weston in 1850 and was a blacksmith for over 40 years. The shop was later moved to South Station Street. He died in 1921.
6. Swing Bridge on the Humber
One of the earliest bridges that connected Weston to Westmount. This was not the bridge wiped out in Hurricane Hazel but a much earlier one.
7. 36 South Station Street
First a house, then a store, then a constituency office for MP Mike Sullivan. A member of the NDP party, Mike came into power in 2011 until 2015. The building was torn down in 2025 to make room for a condo development.
8. Weston Community Coalition
A small number of people that were involved in getting what would become the UP Express to stop in Weston, to not close the streets, and to be electrified. Started out as the Blue 22 Group. From left to right: Mike Sullivan, Luisa Bada, Doug King, Cathy Harris, Dan Harris, Suri Weinberg-Linsky, Faisal Hassan – MPP at the time – Mary Louise Ashbourne, Cherri Hurst
9. Toronto Carrying Place Trail
This trail is as old as time. Created by Indigenous peoples as an overland route from Lake Ontario to Lake Simcoe, it ran close to the river that supplied a source of food and fresh water. This trail is only one of many running through the area. Part of Weston Road was on that trail.
10. St. John's Cemetery on the Humber
In 1801, John Denison bought land in the Weston area. It was intended as a family burial place where he could bury his young daughter, Elizabeth. This cemetery is still in use today. Only Denisons or their relatives can be buried there.
11. Alexander Pearson
He was the principal of Weston Collegiate Institute for 22 years beginning in January 1914. He was very highly respected and earned the nickname "The Boss." His regime took the school through WWI, the huge growth of school attendance after the war, and the Depression. What made it all work? He liked young people.
12. Corner of Weston Road and Little Avenue
These two buildings are two of the oldest in Weston at this time (2025). The one in front was first used by James Cruickshank Sr. to build carriages and caskets. The small one in the back was where they stored the caskets for his undertaking business.
13. Dr. Charlton and His Bride
William J. Charlton, Weston's first mayor, lived and worked at 89 Rosemount Avenue. He came to Weston in 1885 and married Annie McNally on June 24th. Dr. Charlton was one of Weston's leading citizens as he was involved in everything from the Orange Lodge to Community Council to the Board of Education.
14. Watching the Air Show
On July 14, 1910, Count De Lesseps flew his Bleriot monoplane from the Trethewey airfield (Jane and Trethewey) down to the lake and back again. The journey took thirty-six minutes, to fly twenty-four miles, and was seen by many all over the city. He landed safely amid cheers and god will. (Picture from the City of Toronto Archives)
15. Weston is 100 Years Old
In 1981, Weston celebrated its 100th Anniversary. The Weston Historical Society held parades, draws with prizes, and many other events to celebrate.
16. Turning of the Sod
In 1869, Prince Arthur, the Duke of Connaught turned the sod for the Toronto Grey and Bruce Railway. This took place at the north end of Weston by Oak Street, where the new narrow-gauge track left the Grand Trunk track and veered off on its own.
17. Car License Lineup
On the east side of Main Street (Weston Road), just south of Lawrence, in the 1950s, motorists line up for last-minute license renewal. There were notices in the paper for weeks prior to the deadline, but people still left it to the last minute. Some things don't change. The office was in the back of the Bank of Nova Scotia building with the Baptist Church south of it.
18. World War II Work
Betty Pink, Audrey Tomlinson, and Della Day load full Victory Bags that were received from Weston stores, so they could then be taken to a place for sorting. According to the lists on the bags, everything from paper to rags to metal, and then some, was salvaged for the war effort.
19. John T. Pears House
This windmill was perched atop the garage belonging to the house at 2400 & 2402 Weston Road. It was built around 1923, on land that was owned by the Weston Golf and Country Club. John Pears was a builder, and he designed the house in two stages.
20. Baker's Towing
Along with a local taxi service, the Baker family supplied towing and garage work. The garage was situated just north of Weston at 500 Main Street North, while the taxis were located all over town for convenience. This picture was taken in August 1957.
21. All Around the Town
From left to right, top to bottom: 180 Queens Drive – Councillor Oliver Master's house; 2 King Street Crescent – Dr. Charlton's first office; Central United Church – on the corner of King and Weston Road for over 200 years; St. John's Anglican – right after it got moved to Weston Road about 1894; Clubhouse of the Weston Golf and Country Club. From a pamphlet called Weston, A Good Town to Live In.
22. Christmas in Weston
Looking north-east up Main Street North (Weston Road). The Christmas trees are waiting for the customers coming out of Oldman Hardware, the Dominion Stores or perhaps Inch's Drug Store. These were all businesses that were in Weston for some time.
23. Ice Storm of 2013
The December 19th storm was a result of a warm front from Texas mixed with the cold air mass from Eastern Canada. The storm officially dissipated by December 23rd, but there were prolonged impacts. This picture was taken on King Street. The ice was so aggressive that trees were more ice than tree.
24. Dr. T. A. Carpenter
Dr. Carpenter lived and worked out of his home/office at 125 Rosemount Avenue from 1936 to 1985. His wife Eva was the organizer and first president of the Humber Memorial Hospital Ladies' Auxiliary. She had a wing named after her.
25. Laying the Cornerstone
Joseph Burr Tyrrell, the famous explorer and dinosaur man, laid the cornerstone for the new extension of Central United Church.
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