There are summer events, and then there are the occasions that become social calendar staples. The Greenwood Stakes has firmly established itself as one of Toronto’s most stylish annual events, bringing together the excitement of live thoroughbred racing with elevated fashion, gourmet dining, music, and an unmistakably vibrant atmosphere at Woodbine Racetrack. What began as a fashion-forward celebration has grown into one of Canada’s premier race day experiences, where dressing for the occasion is just as important as picking a winning horse.
This year, I had the pleasure of experiencing Greenwood Stakes from a Homestretch Suite, graciously hosted by Blandin & Delloye. Overlooking the track, the suite offered one of the best vantage points in the house to watch the day’s thrilling races while enjoying exceptional hospitality in an intimate, luxurious setting.
The VIP experience was elevated further by a menu curated by Chef Patrick Kriss and the acclaimed Alo Group, featuring refined takes on comfort food that perfectly complemented an afternoon of champagne, conversation, and racing. Between races, guests explored fashion activations, enjoyed live entertainment, and soaked in the lively energy that has become synonymous with Greenwood Stakes.
Race Day Style
| L-R: Gauthier Torres – Blandin & Delloye Montreal, Steve Perigny – Blandin & Delloye Ottawa, Alrick Verner, Sashien Godakandae – CEO Enigmatic Group of Companies | L-R: Alrick Verner, Dwania Peele – Executive Director, Canadian Small Business Women, |
Of course, no race day is complete without the fashion.
Greenwood Stakes has become one of the few Canadian events where guests truly embrace the tradition of race day dressing. Statement fascinators, elegant hats, colourful dresses, impeccably tailored suits, and polished accessories transformed Woodbine into a runway of personal style. Whether classic and sophisticated or bold and contemporary, attendees embraced the occasion with creativity and confidence.
| Tolu Oyetunji – Milliner at Coral Earth Finery | Cappelleria Bertacchi hats and fascinators on-site |
One of the event highlights was the Style Stakes, hosted by Gotsyle where guests competed for the coveted Best Dressed title and the chance to win a $1,000 Gotstyle shopping spree.
More than a Day at the Races
L-R: Sashien Godakandae, Praveeni Perera – The Weekend Fashionista, Alanna Loewen, Nick Bradbury
For those new to horse racing, Greenwood Stakes offers an approachable introduction to the sport. Guests can place friendly wagers, cheer on their favourite horses, and experience the excitement that builds with every race, all within an atmosphere that feels more like a luxury summer festival than a traditional day at the track.
It’s this seamless blend of sport, fashion, entertainment, and hospitality that makes Greenwood Stakes such a standout event. Whether you’re attending with friends, entertaining clients, or celebrating a special occasion, the experience offers something for everyone.
For lovers of timeless style, unforgettable experiences, and the thrill of race day, Greenwood Stakes continues to prove why it has earned its reputation as Toronto’s most fashionable summer tradition.
