Canada’s era of the suburbs was launched by a couple of Shipps. 

In 1950, a 24-year-old Harold Shipp was driving along the QEW past the apple orchards near Cawthra Avenue when a vision appeared in his mind’s eye.  

The post-war baby boom was in full swing and young Harold was a new, second-generation builder.  

His father Gordon Shipp had made a name for himself building homes in the family’s home base of East York, before expanding to Etobicoke and when Harold turned 20 his father renamed the business G.S. Shipp and Son. 

Now Harold was ready to make his name, but he didn’t simply want to build homes. 

He wanted to build a whole town and he already had a name picked out, inspired by the orchards near the highway: Applewood Acres. 

On January 21st, 1951 – Harold’s 25th birthday – he and his father purchased 23 acres south of the QEW for $43,000. 

This is where the Shipps paved the first street, Applewood Road, and got to work building their first 108 homes. 

Harold, a natural showman, knew he needed to market Applewood Acres to families in Toronto that were looking for a bit more space, perhaps a garage, and a neighbourhood grocery store, park and school.  

Applewood Acres had something for everyone – and he needed to catch the attention of potential buyers by going to where they were, rather than expecting them to find him. 

Harold built a model home, placing it amidst an orchard in bloom and in sight of the QEW as families drove by. He furnished it with life-sized mannequins – a dad, a mom and a couple of kids – to encourage motorists to envision themselves in the home.  

Once the apples were gone, Harold put a big red bow around the home to suggest the best Christmas gift for the family would be a new home in Applewood Acres. 

He took out full-page ads in Toronto newspapers, the first home builder to do so.  

Harold even took the skies, renting airplanes to fly advertising banners above the city. 

Sales went through the roof. Young families in Toronto were eager to purchase a single-family home on a large lot. The houses ranged in price from $16,000 to $18,000.  

The Shipps sold 126 homes in 10 days.

Gordon and Harold Shipp

Father and son, Gordon and Harold Shipp. (photo courtesy Mississauga’s Legends Row)

After Applewood Acres, the Shipps built Applewood Heights and Applewood Hills, across an area that stretched all the way north to Burnhamthorpe and extended from Cawthra to Etobicoke Creek. 

The Shipps ended up building close to 900 homes on either side of the highway – along with a neighbourhood school, parks and the Applewood Village Shopping Centre. At the time it was the largest single subdivision built by a family developer in Canada.  

In 1955 father and son built 300 homes in the Credit Woodlands and later that decade added an additional 400 homes to their growing portfolio, this time in Streetsville. 

It was around this time that Harold came up with his most audacious promotion yet. 

In addition to being a home builder, Harold also co-owned the Applewood Chevrolet Oldsmobile Cadillac dealership. 

One day he placed three cars on the roof of three model homes – one car for each roof. When the local planning commissioner told him he needed to remove the cars because they violated a sign bylaw, Harold refused. 

The cars weren’t billboards, he argued.  

The cars stayed and photos of the stunt were published as far away as Japan. 

Then Harold got to work on the centre of the new city. He began to assemble farmland in the area north of Burnhamthorpe and west of Hurontario.  

Just as the new Square One shopping mall was opening its doors in 1973, Harold built a 26-storey, 400-unit apartment building, the highest high-rise in the soon-to-be City of Mississauga. 

He also built Mississauga’s first high-rise commercial development 1978, an office park known as the Mississauga Executive Centre. Four towers of light grey mirrored glass that ranged in height from eight to 18 stories located across from the City of Mississauga’s original City Hall and Square One. 

Harold’s final audacious plan was to build a new domed stadium for the Toronto Blue Jays and Argonauts – in Mississauga. Pitched in 1982 as part of a design competition launched by Ontario Premier Bill Davis, the Trillium Dome was to be a 65,000-seat stadium surrounded by concentric rings for parking and a mix of residential and commercial development. 

It was to be located at the intersection of Hurontario Street and Highway 401.  

Mississauga-based architects DAF Indal called the retractable dome the ‘Stardome’, a reference to the star shape created when the roof was open. 

In the end, Mississauga’s bid was rejected in favour of a site in Downsview, which also was eventually rejected in favour of surplus land at the foot of the CN Tower where the SkyDome, now Rogers Centre, was built. 

Harold Shipp died in 2014 and later that year was inducted into Mississauga’s Legend’s Row. Shipp Drive, which runs north of Hurontario Street between Rathburn Road and Robert Speck Parkway is named in honour of the man who brought us the ‘burbs.

You can hear more stories about the people and events that helped shape Mississauga via our podcast, We Built This City: Tales of Mississauga, available on your favourite podcast platform or from our website. 

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