April 25th & 26th
How It All Started
WineFest at St. Michaels has deep roots in the community. Since 2010, we have proudly served as the organizer and manager of what is WineFest at St. Michaels.This year marks our 17th year of hosting the event.WineFest is managed by a charitable organization, and we are proud to consistently support multiple charities on both sides of the Chesapeake Bay. Giving back to the community has always been central to our mission.
From VIP-Only to Town-Wide Celebration
In 2010 we started Winefest as a town wide celebration of great wines and wonderful foods throughout the town. From 2020 through 2024, we were required to host the event as a single-location, VIP-only experience. The COVID impact primarily limited our ability to draw both volunteers and large crowds to St. Michaels.
Beginning in 2025, WineFest returned to its full vision as a town-wide event, utilizing both licensed venues and non-licensed shops throughout St. Michaels, which host Maryland wineries for the weekend.Today, WineFest once again transforms the town into a walkable tasting experience.
The 2026 Experience
This year’s event will feature:
-
At least 5 large tasting venues plus several MD wineries strategically located throughout town
-
Domestic and international wines
-
200+ different wines to sample
From boutique international producers to local Maryland favorites, WineFest offers an extraordinary range of wines in one unforgettable weekend.
The Best Value:
VIP Sunday Ticket
For those looking to maximize the experience, the VIP Sunday Ticket offers unmatched value.
This ticket includes:
-
Tastings from 11:00 AM – 5:00 PM on Saturday and Sunday
-
An exclusive 3-hour VIP event on Sunday
-
A $75 wine purchase coupon
VIP guests will have access to a curated selection of at least 40 premium wines, ranging in price from $25 to over $150 per bottle.
It is, without question, the most comprehensive and rewarding way to experience WineFest.