Winefest at St. Michaels

Winefest at St. Michaels WineFest at St. Michaels is our joyful celebration of wines from around the world! WineFest at St Michaels is having a "cellarbration"!

Since launching in 2010, we’ve grown this event year after year, creating an experience that’s perfect for both seasoned wine enthusiasts and curious beginners. Join us April 26th and 27th 2025 in beautiful St Michaels, Maryland!

08/13/2026

✨TODAY’S THE DAY! ✨

Our Watermelon Mixology Class tickets officially go on sale TODAY! And this one is going to be a good one. 🍉🍹

Comment “WATERMELON” below and we’ll send you the PayPal ticket link! 🎟️

🍉 Friday, August 28th
🍉 7–9 PM
🍉 Hosted by our faves at The Old Brick Inn
🍉 3 handcrafted cocktails
🍉 Your own cocktail shaker to take home
🍉 Watermelon-inspired light fare

Join us on the patio for a fun, hands-on evening of shaking, sipping, and learning how to make your own cocktails! 🍹

Seats are LIMITED, so grab yours before they’re gone! 🍉✨

IYKYK… you don’t want to miss this one.

Consider this the first tasting. 🥂 A little glimpse into a weekend well-spent in St. Michaels. More to follow!
05/06/2026

Consider this the first tasting. 🥂 A little glimpse into a weekend well-spent in St. Michaels. More to follow!

WineFest weekend is officially wrapped 🍷Thank you to everyone who came out and made it what it was. From the waterfront ...
04/27/2026

WineFest weekend is officially wrapped 🍷

Thank you to everyone who came out and made it what it was. From the waterfront at Foxy’s Harbor Grille to the rest of town—it was a great weekend with great people.

More highlights coming soon!

If you have already purchased your tickets please pick up your wristband and tasting lanyard/glass at the ticket booths ...
04/25/2026

If you have already purchased your tickets please pick up your wristband and tasting lanyard/glass at the ticket booths near the elementary school or Foxy’s Harbor Grille.

WineFest Weekend is here!The tents are up, the wine is ready, and the weekend everyone’s been planning for is finally he...
04/25/2026

WineFest Weekend is here!

The tents are up, the wine is ready, and the weekend everyone’s been planning for is finally here. Multiple stops throughout town, 250+ wines to try, food, and one waterfront stop at Foxy's Harbor Grille you won’t want to miss.

Come for an hour or stay all afternoon—walk through, find a favorite, grab a bite, and let the day unfold from there. It’s meant to feel easy.

If you have purchased tickets, pick up your wristband and tasting glass at the ticket booths.

Haven’t gotten your tickets yet? No problem. Tickets are available at the ticket booth! 🎟️

04/25/2026

Winefest at St. Michaels starts Saturday at 11.00 —but why wait? 🍷

🌟Join us today and all weekend for lunch, dinner, and a little “pre-tasting.”
Small-estate Greek wines, unique pours, and something delicious on every plate.

Trust us—it’s worth getting a head start.

04/24/2026

We have extended online ticket sales until 10am.

After 10am, tickets will be available for purchase at the gate this weekend. 🎟️

The wine is in, the tents are up, and the countdown is on. 🍷Whether it’s a crisp Maryland white or a bold global red, we...
04/23/2026

The wine is in, the tents are up, and the countdown is on. 🍷

Whether it’s a crisp Maryland white or a bold global red, we’re ready to pour—rain or shine. This year, don’t just taste history, be part of it at The Judgment of St. Michaels, our exclusive blind tasting hosted every 45 minutes at the Old Brick Inn.

What to expect:

Fully Tented: We’re covered and ready for a perfect weekend.

Stock Your Cellar: Love what you sip? All wines are available for purchase on-site.

Easy Access: Parking is at the schools right by the ticket booth.

Grab one of the final tickets at the link in our comments. 🎟️

If you’ve been waiting for the right moment to join us, this is your window. Online ticket sales end tonight at 11pm!Fro...
04/23/2026

If you’ve been waiting for the right moment to join us, this is your window. Online ticket sales end tonight at 11pm!

From the first pour to the final sunset, this is about more than just a ticket… it’s about an atmosphere that’s impossible to replicate.

What’s Waiting for You:

The Full Selection: Access 250+ wines spread across multiple venues.

Atmospheric Vibes: Wander through St. Michaels and enjoy its coastal charm.

Curated Moments: Whether you’re looking for a relaxed afternoon or a more elevated experience, there’s a path designed for your style.

You don't need to overthink it. We’ve ensured that joining the festivities is as effortless as the day itself. Experience the exceptional pours, artisans, and delicious food at a price point that feels just right.

Lock in your plans today and get ready for the kind of day you’ll be glad you said "yes" to.

That “I have my tickets” glow. Saturday VIP is gone. General Admission is moving fast. Don’t wait for the weekend to fin...
04/22/2026

That “I have my tickets” glow.

Saturday VIP is gone. General Admission is moving fast. Don’t wait for the weekend to find out what you missed. 🥂

Address

Talbot Street
Saint Michaels, MD
21663

Website

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