Toronto Officially Gets A Derby With The Greenwood Stakes On May 26

Photo: greenwoodstakes on Instagram 

Although the Kentucky Derby is world famous and Vancouver has already been home to the Deighton Cup for ten years, Toronto is now slated to officially welcome the first ever Greenwood Stakes Derby this Saturday, May 26. The derby, which is open to guests aged 19 and up, will feature a horse race, along with signature cocktails, arts and fashion. The event takes place at Toronto’s Woodbine Racetrack, on the Greenwood Raceway, which was officially launched in 1874. Although we have since found our way into the 21st century, the event promises to introduce the old world entertainment of horse racing to a new generation.

Greenwood Stakes has also partnered with the for-non-profit Motionball, which also aims to introduce a younger generation to the Special Olympics through social events. The derby is only one of the 30 events in 18 Canadian cities that Montionball partners with. The organization donates to the Special Olympics Canada Foundation to provide more opportunities and break down barriers for Canadians with disabilities.

Photo: greenwoodstakes on Instagram 

The Style Stakes Best Dressed contest will award one man the Gallant Sartorialist and one woman the Belle Du Jour. These titles come with a $500 cash prize and the designation of Greenwood Stakes Style Ambassadors for the following year. The five judges include Elise Purdon, the founder of silk loungewear brand ELISE, Lowell Hall, a PR specialist, Kevin Gardiner, manager of the Indochino Square One Showroom, Melissa Austria, founder of the men’s lifestyle concept store Gotstyle, and Donna Yasmeen, an influential creative director and stylist. As we come off the high of the Royal Wedding and the beauty of the extravagant hats and the feminine frocks, this event may be ideal for flaunting your best derby fashion. 

Meanwhile, the outskirts of the track are set to offer a Rose-All-Day Garden, a Cocktail Jockey Showcase featuring some of Toronto’s top mixologists, and a DJ tent hosting the performances of Conor Cutz, Eric Carver, and Simon Jain.  Although the Greenwood Stakes is making an effort to appeal to a younger generation, the derby claims to offer a premium scotch lounge, a retro photo booth, art on display, and of course the ability to bid on the horse races. As well, the Toronto natives the Birds of Bellwoods, who recently took part in Canadian Music Week, will be playing live.

For those looking to purchase tickets for the Greenwood Stakes, individual festival tickets are priced at $75 and will offer access to all of the activities. For more information and details about pricing, visitors can check out the event’s website at