St. Michaels’ Weekend of Festivals Appeals to the Discerning Palate

Sure, it’s always a great time to head to St. Michaels. But the weekend of April 27-28 is particularly special with three fun events coinciding.

Wine enthusiasts will enjoy this year’s VIP-style WineFest at the Old Brick Inn, beginning Friday evening and lasting throughout the weekend. The 2024 WineFest is a seated, curated version of the town-wide festival from years past.

The tasting format allows for 10-12 separate wines during each tasting (there are two per day), allowing attendees to discuss flavor profiles with each other and accomplished sommeliers. Wines are exclusively chosen from Italy, France, Spain, the West Coast of the United States, and South Africa.

Besides the tastings, attendees will be educated in terroir integrity, the impact of weather on grape yields, cultivation techniques, and vinification. Special guests will be on hand to guide you through the various characteristics of each grape’s profile, providing an intimate understanding of a single bottle of wine.

Tickets for the event are priced between $30 and $200, with VIP options and discounts on wine purchases included.

After imbibing, plan to stick around downtown St. Michaels for the Taste of St. Michaels Tasting Crawl on Saturday between 11 a.m. and 4 p.m. It takes places throughout the town’s quaint downtown streets. The Tasting Crawl opens local restaurants and businesses including shops, restaurants, cafes, and much more. Tasting venues will have food and drinks for purchase (bring $1 and $5 bills—prices are reasonable). You can build your own bloody Mary at The Fool’s Lantern, or you can go for a run with the St. Michaels Running Co. You might want a single glass of good wine at the Italian-inspired Simpatico, or you might prefer a bottomless mimosa at The Galley.

St. Michaels is one of Maryland’s favorite towns for a reason, and this weekend will bring out all the stops. So don’t be like the Brits and overlook such a wonderful town on the Eastern Shore.