Saturday, May 2, 2026 | 10:00pm – 7:30pm
The 151st Kentucky Derby is almost here, and there’s no better place to watch the Run for the Roses than Blue Sky Vineyard, glass of Illinois wine in hand, surrounded by our signature Tuscan atmosphere.
Derby Hat Contest (Yes… there are prizes!)
When it comes to Derby Day, the race isn’t the only competition. Wear your most beautiful, bold, or totally unforgettable Derby hat for a chance to win:
1st Place: $75 Blue Sky Gift Card
2nd Place: $50 Blue Sky Gift Card
3rd Place: $25 Blue Sky Gift Card
Whose Horse Will Win?
Before the race begins, each guest can grab ONE FREE ticket featuring a participating racehorse name and position. If your horse wins the Kentucky Derby… YOU win a $15 Blue Sky Vineyard Gift Card!
Live Music | 2–5 PM
Plan C will keep the party going all afternoon with their fantastic blend of Americana/Blues/Celtic & Originals.
Limited Derby Day Merch
We’ll have our souvenir Derby Day wine glasses and event t-shirts available while supplies last, and trust us, they go fast.
This is one of our most-loved events of the year. Don’t wait! Share it, add it to your calendar, and make plans now.
(Gift cards may be used toward gift shop & food menu items.)
