What it was like creating Fashion Illustrations for Canada’s most prestigious racing event at Woodbine Racetrack!
On Saturday, August 16th, 2025, I had the privilege of attending Canada’s most prestigious championship—the King’s Plate at Woodbine Racetrack in Toronto. This incredible event draws visitors from all over the country and offers an unforgettable experience filled with high fashion, fine food and drinks, live music, and breathtaking races.
This year was extra special because I was commissioned by Woodbine Entertainment as a live artist to create Guest Sketches in the Paddock Party area. My role for the day was to collect betting cards and capture each guest with my signature live fashion illustrations—a unique keepsake they could take home.
The entire day felt straight out of a fairy tale. Guests arrived in their finest attire—dapper suits, glamorous dresses, elegant hairdos, and the most creative fascinators. For someone like me, who loves both art and fashion, it was a dream come true. The best gift you can give a fashion illustrator is extravagant looks, and this event delivered in the most spectacular way!
With 13 races scheduled, the day stretched from 11:00 a.m. to 8:00 p.m., and my team and I were there throughout, I sketched while they connected with guests. The energy was absolutely electric. People loved the Live Sketching station so much! My setup was simple—just an iPad Pro, phone, my trusted printer, and packaging supplies—but it drew in crowds. At least 75 people stopped to place bets after spotting our activation. By the end of the day, I had sketched more than 110 people in nine hours—my personal record!
The sweetest part was that even if someone lost their bet, they still left with a keepsake they could cherish forever.
As a live event illustrator, the most rewarding part of the day was seeing guests’ reactions. Many stood in awe, admiring the wall of freshly made sketches, their eyes lighting up when they spotted their own. Those smiles and moments of surprise are why I do what I do.
At around 5:30 p.m., we stepped away from the station to watch the main event—the magnificent King’s Plate Race. Huge congratulations to Mansetti the horse, trainer Kevin Attard, jockey Pietro Moran, and the Ulwelling brothers on their impressive win! This was my very first live horse race, and it was beyond thrilling to witness.
We wrapped up with the final race around 8:00 p.m. under the most perfect summer evening sky.
As a Toronto event artist, I’m passionate about capturing the essence of special moments, whether it’s a wedding, corporate event, or luxury celebration. Guests may have taken home a sketch, but I took home the memory of their joy, our conversations, and an unforgettable day at the races.
If you’d like to learn more about my live illustration services in Toronto or commission a custom fashion sketch, feel free to reach out—I’d love to help you preserve your memories in a unique and artistic way.
Don’t forget to check out my video recap of the day!
Tehremy 