Greenwood Stakes

The elegance of the Royal Ascot meets the excitement of the Kentucky Derby with the introduction of the Greenwood Stakes – an afternoon of high stakes horse races, fashion, art installations, mixologist competitions, live music, gourmet food and lawn games set to kick off the summer season in style in Toronto.
Celebrating the 10th anniversary of the Deighton Cup – dubbed by press and attendees as Vancouver’s biggest fashion and social affair of the summer, attracting more than 5,000 people every year – event producers Parade Agency and the Social Concierge are launching its sister event in Toronto, the Greenwood Stakes.

The inaugural event takes place Saturday, May 26, 2018, from 12 – 7 p.m. at Woodbine Racetrack. Sounds of hurried thumping hooves and people excitedly placing bets will set tone of the day, while the centerpiece will be the running of 10 thrilling thoroughbred stakes races, with post time of 1 p.m.
Named in homage to the 19th century Greenwood Raceway that had its heyday in Toronto’s roaring 20’s, the event will bring out the city’s see and be seen crowd clad in bespoke seersucker suits, fascinators and Southern Belle-inspired finery to take part in the festivities of a day at the track.

Drawing on signature elements of the Deighton Cup, the Greenwood Stakes is bringing two popular competitions to Toronto: the Style Stakes Best Dressed Awards and the Cocktail Jockey Mixology Showcase.

The Style Stakes Best Dressed Awards challenges attendees to step up their style game and push the fashion envelope for a chance at one of two $500 cash prizes and to become Greenwood Stakes Style Ambassadors in 2019. Notable fashion industry judges will select 10 finalists (five women and five men), who will show off their ensembles on stage. The judges will then award the coveted Belle Du Jour and Gallant Sartorialist awards, respectively.

The Cocktail Jockey Mixology Showcase will see five of Toronto’s top mixologists in a head-to-head competition to shake up the ultimate twist on a classic cocktail. The winner will earn bragging rights and their winning cocktail will become a signature cocktail at the Greenwood Stakes.
Tickets start at $75 and go on sale Tuesday, March 27 at A portion of proceeds from all ticket sales will benefit motionball for the Special Olympics Canada Foundation.