Greenwood Stakes Is Toronto’s Most Stylish Day at the Races

This daytime festival will see thousands of derby revellers, as well as races, live performances and bottle-popping action!
greenwood stakes toronto

A day at the races is cool again! Toronto’s most fashionable track-side event is officially back on Saturday, September 9th 2023 for its 4th edition of derby action at Woodbine Racetrack. Each year, Greenwood Stakes is bigger and better with the most creative outfits, excited guests, and thrilling races, of course!


This year, you will be able to watch a stacked schedule of adrenaline-pumping horse races to enjoy and bet on! Will your pick win?

Food & drinks

The perfect derby snacks must accompany a day as stylish as this! On-site, you can explore options of lunches to satisfy your afternoon appetite and get your geared up for more fun. Food Dudes is supplying the menu to elevate the occasion.

There will also be a number of bars all around the venue featuring craft cocktails by Tito’s Handmade Vodka, Cointreau, and Rémy Martin; Stella Artois beer; pours by Cottage Springs, and more!

Style Stakes by GOT STYLE

Aside from the horse racing and menu offerings, style is a huge part of Greenwood Stakes. If you’re going, dress to impress and enter to be a part of The Style Stakes. Each year, a winner is awarded a $1000 prize from GOT STYLE Men’s & Women’s Wear and recognized as ‘best dressed’ for the event!


If the thrilling horse races and betting wasn’t enough to keep you entertained all day, there’s also live musical performances by recognized local artists. DJs and more all around Woodbine Racetrack to ensure there’s lively fun around every corner.

Attend like a VIP

Get the whole crew together and made it a day! Festival passes and group tables are currently sold out, but you can still snag a Last Minute Trackside Suite. These consist of:

  • All the inclusions of the Festival Pass for 10 people
  • A reserved section and a VIP table for you with seating for 10 guests
  • Suite branding to showcase your involvement
  • The Trackside Suite location provides unparalleled proximity to all the racing
  • A chic atmosphere outdoors sets the mood for the day’s festivities
  • 3 Bottle of Piper Heidsieck Champagne + 10 pack of Stella Artois
  • Private server for the day handling your suite

Need the perfect outfit now that we’re just around the corner from Greenwood Stakes? Head here to read up on all the best Canadian brands to shop!

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