Next up: Festival Stakes Day, Sat 28 Nov
1 upcoming race day
The King's Plate at Woodbine leads a short summer season of race days worth dressing for.
flagshipSat 14 Aug 2027
Woodbine Racetrack, Toronto
Canada's showpiece race day for hats: Woodbine's own guide says 'start at the top' with oversized brims, fascinators and bold fedoras, worn with bright summer dresses and lightweight suits. Woodbine bills it as Toronto's can't-miss social event of the summer.
The club has not published the date yet. Each moves onto the calendar when it does.
A Sunday in late September (27 Sep 2026)
Woodbine Racetrack, Toronto
Final leg of the Canadian Triple Crown; no fashion programme found.
A Saturday in late August (22 Aug 2026, 97th running)
Century Mile Racetrack and Casino, Edmonton (Nisku, by Edmonton International Airport)
Western Canada's biggest race day. There is no dress code, but the crowd dresses Kentucky Derby-style with hats and fascinators; the ticket page sells 'an afternoon of excitement, entertainment, fashion and more'.
A Saturday in early October (3 Oct 2026)
Woodbine Racetrack, Toronto
Woodbine's autumn turf championship day; no fashion programme found. Autumn coats, tailoring and felt hats suit the weather.
A Saturday in late June or July (11 Jul 2026; 21 Jun 2025)
Woodbine Racetrack, Toronto
A 19+ fashion-and-music race day built around dressing up; the organiser's FAQ says 'Greenwood Stakes is a day to dress your finest. Grab your chicest fascinator and best bow-tie.' The Style Stakes best-dressed contest is the centrepiece.
First Monday in August, the August long weekend (3 Aug 2026), evening card with 7:30pm post
Assiniboia Downs, Winnipeg
Winnipeg's one dress-up race night. In 2025 the track invited fans to wear a fancy Derby hat or their best Derby attire and be photographed at the Manitoba Derby backdrop for a prize draw.
A Saturday in late July (25 Jul 2026; 27 Jul 2019)
Century Downs Racetrack and Casino, Calgary (Balzac)
Calgary's dress-up day at the races: the organiser calls it 'a true celebration of old world leisure and sophistication' with 'luxury, horse racing, fashion, and food & drink', and quotes a review that it is 'inspired by the gentrified atmosphere you might find at the Kentucky Derby'.
Early September; Labour Day Monday in 2026 (7 Sep 2026), a Tuesday in earlier years (9 Sep 2025)
Fort Erie Race Track, Fort Erie
Fort Erie's biggest day and the second jewel of the Canadian Triple Crown; the track sells it as 'family-friendly festivities'. No dress code or fashion contest is published.
A Saturday in mid-September (12 Sep 2026)
Woodbine Racetrack, Toronto
Woodbine's top international race day; no fashion programme found. Early-autumn tailoring and smart dresses fit the hospitality rooms.
A Sunday in mid-July (19 Jul 2026), same card as the Plate Trial
Woodbine Racetrack, Toronto
A racing-first day; no fashion programme found. Smart summer race wear suits the Woodbine Club and Level 4.