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Derby Day at Woodbine Racetrack

May 2, 2026

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Event Details

Saturday, May 2, 2026 @1:20 p.m.

Woodbine Racetrack – 555 Rexdale Boulevard, Toronto ON

Free parking

Free Entry

About

Get dressed in your Derby best for spring’s most stylish day at the track as we celebrate the Kentucky Derby at Woodbine Racetrack.

Enjoy a thrilling afternoon of live Thoroughbred racing beginning at 1:20 p.m., including the Whimsical Stakes (Gr. III) presented by Crown Royal. As the day builds toward racing’s biggest moment, guests can also watch and wager on the Kentucky Derby broadcast live from Churchill Downs, with a post time of 6:57 PM.

Hats, fascinators, and Derby-inspired attire are highly encouraged.

WHAT TO EXPECT

Live DJ between races to keep the energy up all day
Photo moments: photo op on our Galleria Level, and a rose petal GIF booth on Level 3
Claw Machine with Fun Prizes on Level 3
Portrait Sketches on Level 3
Special menu features + classic Mint Juleps
Dining Rooms – SOLD OUT

WAGERING MADE EASY

Additional live tellers throughout the venue
Wagering Ambassador in dining areas
Roaming Brand Ambassadors on Levels 2 & 3 to help you get started
$10K in Golden Ticket giveaways – your chance to win when you place a tote machine bet
HPIbet Pins to showcase who your Kentucky Derby horse pick is!
A Digital betting guide to help you make your picks!

BONUS

A feature contest to win Derby Day 2027 tickets.

On Track Experiences

GOLDEN TICKET

ENTER TO WIN YOUR SHARE OF $10,000 IN BET VOUCHERS*

Place a wager at any self-serve tote machine on Derby Day for your chance to win.

*Must be on-site, May 2, to participate.

ENTER TO WIN A 2027 KENTUCKY DERBY PRIZE PACK*

Prize includes 2 tickets to the 2027 Kentucky Derby, welcome package and access to exclusive spaces.

*Must be on-site, May 2, to enter.