Why You Should Attend the WineFest at St. Michaels

The Wine Festival in St. Michaels, Maryland on the last weekend in April
Oh yes, you’re going to taste A LOT of wine during the WineFest at St. Michaels.


Get ready people, one of my favorite events takes place every year on the last Saturday and Sunday in April, meaning it’s happening soon and you still have time to attend. Here’s what you need to know before you go.

St. Michaels is Awesome

A trip to St. Michaels for the WineFest includes views like this one.


St. Michaels, Maryland, is one of those little hidden gem Eastern Shore towns you probably only hear about if you have family or friends from the Washington D.C./Maryland area. It’s still off-the-radar enough to be quaint, but on-the-radar enough to be filled with fun shops and delicious restaurants, making a lovely weekend destination. Oh, and did I mention it’s located right on the Chesapeake Bay, so add stunning water views and you’ve pretty much got a perfect place to visit even without a Spring wine festival.

The WineFest at St. Michaels

Sure there are wine festivals throughout Virginia, Washington D.C. and Maryland, but I love the WineFest in St. Michaels in particular because the tasting venues are woven throughout the town and there are 14 of them!


Signs for the wine festival in St. Michaels, Maryland
Look for signs like these to find St. Michaels WineFest tasting venues throughout the town of St. Michaels, Maryland.

So instead of cramming into one crowded tent, you can wander through the town, stop into shops, grab a bite to eat (check out my dining recs), then hit a tasting tent, and move onward. Tents are open both days from 12 to 5 p.m. and there are more than 300 wines to sample. With so much happening throughout the town, you can usually find a spot that isn’t super crowded, even with so much going on. There are also shuttle buses that take tasters from tent to tent if you don’t want to walk or are bringing guests who have limited walking abilities. Various ticket options are available for one or two days and start at $85 for Saturday and $55 for Sunday.


Taste Wine throughout the town during the WineFest in St. Michaels


Friday Night at the WineFest at St. Michaels

Each year, the festival starts with a rare and reserve wine tasting on Friday night. This year the event features Marchesi Antinori wines. The Antinori family has been producing wine for over six centuries and is largely crediting with starting the Super Tuscan wine trend with their famous Tignanello wine. That and five other rarely available Antinori wines will be available for tasting and purchase at the event. They will not be available any other time during the WineFest. Tickets to the Friday Night Rare and Reserve Tasting cost $65.

VIP at the St. Michaels Wine Festival

Both Friday and Saturday at the WineFest at St. Michaels have a VIP option available. These tickets include exclusive wine tastings poured by the winemakers, a VIP wine tasting cruise, entry to all the regular tasting venues, and some other perks. The Sunday option—which I’m particularly interested in—includes a vertical tasting of Faustino Gran Reserva Rioja with vintages dating back to the 1980s. VIP tickets cost $150 for Saturday and $110 for Sunday.


Taste so much wine at the WineFest at St. Michaels

Make Sure You Visit Italy

My favorite and one of the more slightly off the beaten path tasting venues is hosted by Simpatico, a gift shop dedicated to items imported from Italy.

Simpatico also offers gourmet food for sampling as well as other goodies during the WineFest.
Some of the other goodies Simpatico offers during the WineFest.

As you might guess, the wine tasting features exclusively Italian wines and is my favorite because you can actually learn a lot about what you do and don’t like with many variations on classic varieties under one tent. In fact, if I happen to stop by here and it’s not too busy, sometimes I try to taste by varietal instead of by table as most tables offer a Sangiovese or Primitivo—why not take advantage of the opportunity if you have the chance?

Taste Italian wines like Chianti at the Simpatico tasting venue at the St. Michaels Wine Festival.
You can also taste many different takes on Chianti in the Simpatico tasting area.

Don’t miss the Zonin table where you can taste a few of my all-time favorites, including Zonin prosecco, Nero D’Avola and Valpolicella Ripasso. As the largest wine producer in Italy, Zonin owns vineyards throughout the country, and offers wines with a wide a range of styles and flavor profiles. Tom from Zonin is also great at demystifying Italian wines if you are actually interested in learning something while you kick back all that nectar of the gods. Fans of sweet drinks should also make a point to sample the Moscato as well as the classic bellinis that are served at the Zonin table. The fresh, fruity peach mix is sold as a gift set with the Zonin prosecco—the set is perfect at home for any brunch party.


Italian wine tasting at the WineFest in St. Michaels Maryland.
Look for Tom and his giant map of Italy. He’ll help you taste your way through the country.

Where to Stay for the WineFest at St. Michaels

Unless you are super coordinated and plan your stay way in advance, you probably aren’t staying in St. Michaels. Stay nearby in Easton, Maryland, which features both chain hotels and bed and breakfasts. It is about a 20-minute drive from St. Michaels, though, so plan a designated driver, or book a dinner reservation in St. Michaels and plan to hang around the town for a while after the festival before driving out of town.

1 Comment
  1. Megan, I am so happy you enjoy the Italian experience at our Simpatico venue, Tom and Dan are returning from Zonin along with our other fabulous Italian importer partners, with a lineup of 82 wines and liqueurs, very excited about our offerings this year, along with Italian foods and more. Grazie Mille for visiting us, see you next weekend! Salute!

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