The Deighton Cup

A day at the races. 

By Yasmine Shemesh

Ladies adorned in their best peeked from underneath wide-brimmed hats as they sipped on chilled mint juleps. The gents, dapper and outfitted in ascots, puffed on cigars while placing bets on their favorite ponies. The brass from the Seattle-based jazz band, Tubaluba, filled the balmy summer air. The Deighton Cup, one of Vancouver’s most playful and stylish summer affairs, took place this past weekend at Hastings Racecourse. Created by friends Tyson Villeneuve and Jordan Kallman of the Social Concierge, and owner of Cocktails and Canapes, Dax Droski, the event is in its fifth and most successful year.

What started five years ago by the trio as a single-day passion project has grown into a weekend festival that draws some 3,000 people. Guests at the Deighton Cup include a wonderful cross-section of generations, from earnest twenty-somethings to seasoned race-goers who remember a time when the Happyland Giant Dipper was torn down. “There are no segregated sections, no people elevated above another,” Kallman says. “Everyone is family and deeply connected. It’s just a really fun time with really great people playing dress up.”

Horse racing was a family pastime for Droski growing up. To honour that family heritage, he sported his grandfather’s watch. “The only day of the year I put it on,” he notes. Villeneuve wore his grandfather’s tie and watch, too, and Kallman carried his grandfather’s pocket watch.

Introduced to the program last year was the Big Smoke, a Friday evening track experience illuminated by lights and accompanied by a pig-roast dinner, bourbon tastings, and complimentary cigars. This summer welcomed the addition of the Julep on the Sunday, a cocktail competition between 12 of the city’s best mixologists and judged by a panel including Jay Jones, Mark Brand, Peter Thomasen from Bulleit Bourbon, and Sandra O’Connell from “Tales from a Bar Stool”. Sean McGuigan from Clough Club claimed first prize, with Alex Black of Hawksworth Restaurant following in second place, and Pidgin’s Robyn Gray in third.

The original stand-alone event, the Thoroughbred, took place on Saturday afternoon. The Deighton, its name an homage to our own notorious gambler and whiskey-lover, Captain “Gassy” Jack Deighton, is itself a tribute to the elegance of eras past, to a time where cats got dressed up to the nines to catch a race. Lamborghinis rested underneath paper lanterns alongside white sofas atop the grassy knoll aptly named the Field of Dreams. A man in braces and pulled-up ankle socks raked the gravel pit for the horseshoe toss. Spectators, perched atop the Veuve Clicquot stage, watched the steeds gallop around the race track in competition. The crown jewel: a vintage repurposed horticultural trophy, circa 1927, engraved every year with the name of the winning jockey and horse from the sixth and final race, as well as the Style Stakes best dressed.

Fashion at the Deighton is just as highly anticipated as the races themselves, a testament to the pageantry surrounding derby culture. Ladies donned tasseled, Gatsby-esque flapper dresses and colorful ensembles finished with lacy gloves, ornate headpieces, and floppy sun hats. Meanwhile, the fellows more than impressed with flat caps, head-to-toe plaid paired with antique mahogany canes, Oxfords, and candy-colored suits.

Miss America Mallory Hagan even came out to play. Beautifully dressed in Joseph Ribkoff with a fascinator designed by local Hive Mind Millinery, it’s safe to say Mallory enjoyed her first trip to British Columbia in style. As the host of the event, she chose the best dressed in the Style Stakes, Praise Vaughn.

Although still young in its years, the Deighton Cup has brought the luxe aesthetics and age-old traditions of racing culture back into Vancouver’s spotlight. On the West Coast, being laid-back is a rule of thumb, but it’s also nice to get dressed up once in a while. As the sign dangling from a tree branch in the Field of Dreams proclaimed, “If the crown fits, wear it.” Here, we all got one.

Published online at www.montecristomagazine.com, August 2013

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