Kentucky Derby Day: Watch Party 

Get ready for the most exciting two minutes in sports, right here in the heart of Boerne!

Whether you are stopping by for a pre-party toast or staying to watch the main event, we are bringing a touch of Louisville luxury to the Texas Hill Country.

The Race Day Experience

We are turning up the excitement for Derby Day with a schedule designed for maximum fun:

• Watch the Race Live: We will have the Kentucky Derby coverage streaming live in the Tasting Room. Come cheer on your favorite horse surrounded by fellow fans.

• Derby Day Watch Party: Make Lost Oak Cellars your official Derby headquarters. We offer a relaxed yet festive atmosphere to enjoy the spectacle.

• Pre-Party Sips: Just stopping by the Mile? Our Tasting Room is the perfect place to kick off your afternoon with a refreshingly sophisticated vibe.

Half-Price Glasses for Headwear

We are celebrating the tradition of the Derby with an exclusive feature just for you:

• Wear Your Derby Hat, Save Big: Any guest who visits us wearing their festive Kentucky Derby hat on May 2nd will receive 1/2 price on a single glass of wine! From elaborate fascinators to classic fedoras, show us your best headwear and enjoy the savings.

Sip, Savor, and Celebrate

While you enjoy the racing, explore the full range of hospitality at our Boerne location:

• Award-Winning Texas Wines: From crisp, chilled whites to our most celebrated Hill Country reds.

• Cocktails & Mocktails: Not in a wine mood? Enjoy our seasonal wine-based cocktails or our refreshing, handcrafted mocktails.

• New Food Menu: Pair the afternoon with gourmet selections from our new food menu, featuring artisanal charcuterie boards, savory shareables, and delicious snacks.

Event Details at a Glance

• Date: May 2nd, 2026 6:00 pm

• Time: Open during regular business hours; Race coverage

• Feature: Derby Watch Party & Pre-Party.

• Promotion: 1/2 Price Glass of Wine for guests in Derby Hats!

Experience the excitement of the “Run for the Roses.” Grab your biggest hat, gather your friends, and head to Lost Oak Cellars for an unforgettable Derby Day celebration!