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Umbrellas touching, the compact foursome looked up at the grand entrance to 150 Laird Dr.

"What does it say?" asked Jane Pitfield. "You can see some lettering there: W… O … R?"

"It says Durant!" Geoff Kettel exclaimed .

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"D-U-R-A-N-T, yes! You are right, Geoff – amazing," Ms. Pitfield replied.

The other two nodded approvingly.

Most Leaside residents know the Neo-Gothic building, built in 1928, was the former head office of Durant Motors of Canada, but since it had played so many other roles since the last car rolled off the assembly line in 1933 – many remember the building as the offices of the Metropolitan Separate School Board in the 1960s and 70s – to find a ghostly typographic trace over the front door was cause for celebration.

Ms. Pitfield, former city councillor, 2006 mayoral candidate, current Leaside resident and editor of the indispensible 326-page book, Leaside (Dundurn Press, 2000), and Mr. Kettel, an award-winning heritage advocate and Leasider, had gathered with Elaine Fujiwara, curator of the "Leaside 100" exhibit, and Tree of Life Video's Anna-Louise Richardson, to do a dry run of their "Layers of Leaside" walking tour on a wet day before making it available to the public.

A few minutes before the discovery at the Durant building, Ms. Pitfield had outlined the rich industrial history of the formerly independent Town of Leaside, which officially celebrated its 100th birthday on April 23, 2013.

"Leaside, at one time, was full of pollution and soot because it was a heavy industrial area," Ms. Pitfield had explained, "and the buses were lined up, bringing people over here [to work]."

It's true: Across from the Durant building, where a faux-Spanish big box mall now stands, is where the Durant and Star models, and Rugby trucks, were put together. Even more impressive was Canada Wire and Cable, which purchased 6.5 hectares in 1912 at Wicksteed Avenue and Laird to build a factory, but switched their focus to munitions during the First World War before a centimetre of wire had been produced. A huge benefactor to the town over the decades, by 1978 CW&C would employ 2,700 people.

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Street names help tell the story: Commercial Road, Industrial Street, Canvarco Road for the Canadian Varnish Company, Research Road, which celebrates the hi-tech work of the Second World War's Research Enterprises, Ltd., and Esandar Drive, which references the initials of the E. S. & A. Robinson's of Canada Ltd.

Of course, in the mind's eye of most Torontonians, the name Leaside conjures up images of quaint Tudor homes on leafy, curving streets. During the tour, which will start at the Leaside branch of the Toronto Public Library (165 McRae Dr.), Ms. Pitfield and Mr. Kettel will take walkers past residential landmarks great and small.

The former 1919 home of the town's longest serving politician, George Wilkinson – sporting the town's only Dutch gambrel roof – will be a stop, and Ms. Pitfield will tell of how Mr. Wilkinson made violins there as a hobby … and how it was recently saved from demolition.

Where Bessborough Drive dead-ends at Howard Talbot Park, the pair will reveal the currently unfolding story of the Thomas Elgie farmhouse, a settler home built in the 1870s. "It's like something out of Gatsby," said Mr. Kettel, gazing at the sweeping circular driveway. Unfortunately, there is also a development application to demolish parts of the house, remove the driveway, and intensify the site.

Speaking of Mr. Talbot, a Leaside mayor from 1938 to 1947, the single-family homes he built in the late-1920s and early-1930s – with their distinctive cantilevered window-box on the side – will be discussed, as will the recent David versus Goliath tale concerning his low-rise Georgian Revival apartment complex on Bayview, south of McRae. A grassroots-against-corporation battle that went all the way to the Ontario Superior Court, the Strathavon, Kelvingrove and Glen-Leven apartment complexes stand today because of neighbourhood passion.

The tour would be remiss if it didn't include homes owned by the Lea family. Both built by grandsons of John Lea (who started the whole thing by purchasing farmland here in 1819), the James Lea home at 201 Sutherland Dr. (1909) is interesting for its lack of a front door; it once sat facing James Lea Lane, which disappeared when the modern road system was built. Similarly, James's younger brother, John Edmund Lea, built a home at 33 Heather Rd., which also faced a lane; since that lane no longer exists either, a front door was installed facing the street in recent years.

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The most important Lea home, however, is only a memory. "Leaside," the octagonal home built by John Lea's eldest son, William (at some point between 1851 and 1854 when he founded the Village of Leaside), was deliberately set on fire by the Canadian Northern Railway in 1913. Despite this act of architectural cruelty – "No one was a heritage person then," lamented Ms. Pitfield – walkers will learn that railways played a major part in the shaping of Leaside beyond the curve of the streets.

Walkers will also hear about the massive aerodrome, the first airmail delivery, the first general store (Perrem and Knight) and former East York mayor True Davidson's "informal edict" to keep the name "Leaside" on any building, park or public space after amalgamation occurred in 1967.

The need for a Heritage Conservation District due to present-day threats from domino-like McMansions, big box malls and overzealous condo developers will also be addressed.

The Layers of Leaside Heritage Walking Tour with Geoff Kettel and Jane Pitfield takes place Sunday, April 28 at 1:30 p.m. Walkers meet at the Leaside Branch of the Toronto Public Library, 165 McRae Dr., where an exhibit by Elaine Fujiwara will be on display. Duration is approximately two hours. The walk will be repeated on Sunday, May 5 as part of the Jane's Walk series. More information is available at

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