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Best in Show Winner at the inaugural Cobble Beach Concours d’Excellence: this 1928 Isotta.DAVID BUCK

The Pebble Beach Golf Links looks west over the Pacific Ocean, the Cobble Beach Golf Resort east over Georgian Bay. That's an unanticipated natural advantage for the fledgling Cobble Beach Concours d'Elegance, with the classic cars arranged in the September morning bliss.

"Facing east, we get the sunrise," Rob McLeese says. "It's just spectacular, the sun coming up over the water, and the cars taking their places on the 18th fairway ..."

Cobble Beach truly has its roots in Pebble Beach where North America's most prestigious concours has been staged for 64 years. Willis McLeese, Rob's father, neither played golf nor owned a classic car but he found inspiration when work took him to the Monterey Peninsula. Seeing a parallel in the scenic geography, in 1998, at age 74, he bought 235 hectares on Georgian Bay. Cobble's golf course opened seven years ago and Willis wanted a concours to complete the resemblance to Pebble. In the months following his father's death in 2011, Rob made it his objective to begin building one of the finer classic car shows in North America. Comedian and car collector Jay Leno observed last month that Pebble's concours "is a wonderful event where a millionaire can compete with a billionaire and win – only in America!"

McLeese, also president of Access Capital, while allowing "we'd love to be a rival to Pebble," believes in building the concours with "baby steps, never trying to do too much." And the quality of entries in the 21 competitive classes this year, following the inaugural show last year, testifies to his goal of incremental annual improvement.

New to the event is a museum class, displaying collector's items seldom seen in the natural light of day. Henry Ford's 1906 Model N, which preceded the Model T by two years, is to arrive from the CCCA/Gilmore Museum in Michigan. The 1867 Seth Taylor steam car, a Canadian breakthrough, is from Ottawa's Science and Technology Museum.

Jeffrey Seigel has bought and sold maybe 100 Ferraris and 2,500 Porsches at Segal Motorcar Co., but he purchased the 1970 Dino 246 GT from Frank Diponzio with the pledge of owning it forever. Over the years, he had appreciatively watched Diponzio restore the car – "so exacting in his work" – and kidded him, too, saying, "You know you're doing this for me." When Diponzio retired, he sold the car to Seigel, who had the restoration completed to a standard that has earned Ferrari certification. "Painting it took three years [because] the Ferrari primer requires so much time to harden," Seigel says.

Two McLaughlin-Buicks score bonus points with those who believe any Canadian concours should salute Sam McLaughlin, the Oshawa buggy maker whose company became General Motors of Canada. Rosemary McLeese, Rob's wife, surely agrees as a descendent of George McLaughlin, Sam's older brother.

While the cars on display this weekend will do the concours proud, the quality of the judges may represent the most significant progress. The 43 scoring cars and three honorary judges have been recruited from 14 states and five provinces. A concours grows in step with its judges: the greater their stature, the more enthusiastically premium collectors vie for invitations.

John Carlson, a chief class judge at Pebble Beach, the chief judge at numerous respected American concours, and chief judge at his native British Columbia's Crescent Beach event, sets a certain standard. Before agreeing to come on board as Cobble's chief judge, he requested a free hand to recruit class judges, "the best of the best from across North America." He also received a commitment from McLeese that the event would be underwritten should revenue from sponsorships fall short of expectations. Receiving that commitment from McLeese, who is developing real estate around the golf course, gave Carlson the confidence that the event would continue to grow.

It's a challenging task to build an event of this stature near Owen Sound, Ont., several hours' drive northwest of Toronto. When Cobble's initial attempt at staging a concours foundered for lack of entries in 2012, Steve Plunkett, a prominent collector from London, Ont., stepped forward after being "bowled over by the setting."

He persuaded the McLeese family to postpone the inaugural until 2013 and, as special adviser, used connections to help bring in some people to give the event credibility. They included emcee Ed Lucas as "so important to creating atmosphere," Wayne Cherry the former vice-president of design for General Motors, and Myron Vernis, who ran the concours at Glenmoor Country Club in Canton, Ohio.

"The family ran the event so well they don't really need my help this year," Plunkett says. "I'll be there competing with two of my Cadillacs," including a 1934 V-16 that won best-in-class at Amelia Island in 2012.

On-site auctions create excitement and generate publicity: auctions at Pebble last month accounted for $399-million in sales. Accordingly, McLeese has invited representatives from RM Auctions, the Canadian firm that sold one Ferrari for $24-million at Pebble, to come take a look.

As a businessman, as well as founder of the concours, McLeese is familiar with playing the long game. He understands the sponsorships will come after two or three years, when the concours is established. Early days, these, but he's looking to the horizon, over the 18th fairway, into sunshine.

Admission for Sunday's concours is $40 for adults, $35 for youths, $115 for a family of four. Saturday's activities are free, with a donation encouraged to the Sunnybrook Hospital helipad project, to which Cobble donated $50,995 last year.

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