Fashion Gambles at the First Greenwood Stakes

The first ever Greenwood Stakes happened at Woodbine Racetrack on Saturday the 26th of May 2018.  This is a fashion event in an equestrian setting.  The festival is being dubbed Toronto’s newest society event at the races.  Big tents, food vendors, music and games took over the Woodbine Racetrack that warm Saturday afternoon until 7 p.m. in the evening.

The event was crowded from 1pm to 4pm as eight hundred guests squeezed into the track-side enclosure at the east end of the Woodbine Raceway Grandstand. This area was made over with faux tropical trees and upscale patio furniture. The central terminal was a cavernous big-top tent that accommodated several HPIBET stations and cold food vendors which is similar to how the place is setup during Queen’s Plate event in July.  Outside the main area there were a variety of vegetarian and meaty sausage distributors, sushi makers and a pork-on-a-bun shop.

The people at this event were the real attraction; almost everyone here was an original and stylish entrepreneur or high profile business executive. Below is Christy Fenn a model and fashion designer, and Richard Carmichael a veteran web marketing strategist in Toronto.

Greenwood Stakes was filled with influencers who make media on Instagram and Twitter. Anyone can see their work by typing #GreenwoodStakes into Google or any social media platform. Here’s a dapper crew playing Jenga with foot long 2x4s at Greenwood Stakes at approximately 2pm. The Angry Orchard cider people had a big spread right beside the track.

Instagram influencers at Greenwood Stakes had all manner of things to photograph and some brought fascinating accoutrements to add to the scene. The lady below had a bird on her hand.

There were hats of all types, and men with stylish vests or suspenders over white cotton shirts. Lots of suit jacket blazers over matching dress shorts (very chic) and deck shoes worn with no socks. Almost all the ladies wore colourful hats or fascinators in their hair.

Hats were mandatory at Greenwood Stakes. Both men and women wore very fashionable designer hats.

Look above. These two gentlemen were NOT country music stars, but in fact stylish hat makers; they are clever craftsmen who make authentic old-school felt hats out of beaver fur.

2018 Style Stakes Best Dressed Awards at Greenwood Stakes

The 2018 Style Stakes Best Dressed Awards challenged the Greenwood Stakes 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.  At 3:30 pm, notable fashion industry judges selected ten finalists, five women and five men to bring on stage and show off their clothing ensembles.

The judges then awarded the coveted Belle Du Jour and Gallant Sartorialist awards, respectively. So who won? The information.

Cocktail Jockey Mixology Showcase saw five of Toronto’s top nightclub mixologists square off in head-to-head competition where they worked on stage to shake up the ultimate twist on a classic horseracing themed cocktail.  The winner would earn bragging rights and their cocktail recipe would become a signature cocktail at the Greenwood Stakes. So who won? This information.  Throughout the compound there were fruit-filled drink stations. Most alcoholic concoctions were ten dollars each and composed of rye, vodka or gin.  The ladies liked champagne cocktails.

Track-side bars lined the promenade and were tailor-made for sharable moments for our Instagram generation.  Toronto’s top mixologists smiled for cameras and shook up their own unique takes on the classic champagne cocktail, the mint julep, and other famous bourbon libations that are commonly associated with horse races.  These upscale bartenders were competing to create the perfect summer refreshment; they were inspired by recipes dating back to the early 1800s.  Led by Cocktail Director Evelyn Chick, the Cocktail Jockey Showcase featured custom cocktails that were handcrafted by Zak Doy (of the nightclub, Figo), Casey Ryan (of Civil Liberties), Sally Gillespie (Pretty Ugly) and Tyler Newsome (of Bar Raval).

The horses were famous too.  Among the runners was the 2016 Queen’s plate winner Sir Dudley Digges, and other celebrity horses that were big winners throughout the years.

They were running to win the $175,000 Grade 2 Eclipse Stakes which is a long-standing tradition that is now, informally, part of the Greenwood Stakes celebration at Woodbine Racetrack. Are You Kidding Me paid $5.60, $2.80 and $2.20. He combined with Melmich ($3.50, $2.40) for a 4-1 exacta worth $13.20. A $1 trifecta of 4-1-2 (Gigantic Breeze, $3.10) paid $16 and a $1 superfecta of 4-1-2-3 (Tizzarunner) returned $122.30. Tiz a Slam, also trained by Attfield, finished fifth while Sir Dudley Digges and Hollywood Critic completed the order of finish.

The Music was also impeccable. There was live music from one of Toronto based folk-rock quartet, Birds of Bellwoods, and popular DJs Eric Carver, Simon Jain and Conor Cutz, who covered a variety of genres including Hip Hop, RnB, Dancehall, Classic and Deep House.

The Art at 2018 Greenwood Stakes Pop-Up Art Gallery was curated by Toronto-based creative director, video producer and clothing designer Meghan Kraft.  The exhibit featured works from emerging Toronto artists including: Alpo Snow, Arturo “Duro the Third” Parada, Briony Douglas, Coup de Tête, and Jacqueline Poirier A.K.A. The Crazy Plate Lady.

Fashion gambled and won at 2018 Greenwood Stakes as $ was raised for charity.