How It All Started
WineFest at St. Michaels has deep roots in the community. Since 2010, the festival has brought wine lovers together in St. Michaels for a celebration of exceptional wines, wonderful food and the unique character of Maryland's Eastern Shore.
WineFest is managed by a charitable organization, and giving back has always been an important part of the event. Over the years, the festival has supported multiple charitable organizations on both sides of the Chesapeake Bay.
WineFest began as a town-wide celebration, with guests moving throughout St. Michaels to experience wines and local businesses. From 2020 through 2024, circumstances surrounding the pandemic required the festival to operate as a single-location, VIP-only event. In 2025, WineFest returned to its original town-wide format, once again creating a walkable tasting experience throughout St. Michaels.
What's New at WineFest This Year?
If you've been to WineFest before, you may be wondering what's different this year after 15+ years of WineFest. We're glad you asked.
This year, VIP gets even better.
For the first time, VIP wines will be featured at two separate venues. On one day of WineFest, you'll spend a couple of hours enjoying VIP wines at one venue, and on your other day, you'll visit the second venue. The rest of each day you'll be able to enjoy the General Admission venues, which are all included.
That means VIP both days!
Instead of having just one VIP experience, you'll now have 4+ hours of premium wine tastings between both days, giving you more time to explore, taste, learn and decide which wines you want to take home.
And there's truly something for everyone: Bubblies, Whites, Rosés, Reds, Ports, Desserts and more.
More VIP Options. More Ways to Enjoy WineFest.
Whether you're a first-time guest or a WineFest regular, we've also introduced more than one VIP ticket option, so you can choose the experience that fits you best. With either VIP ticket, you'll enjoy all of the regular WineFest venues plus a VIP experience each day.
And there's another great perk: wine-buying discounts are included with your VIP ticket.
VIP Ticket: $50 off a $250 wine purchase, redeemable either day.
VIP Black Ticket: Two $75-off coupons, each redeemable on a $300 wine purchase.
Choose the VIP experience and the wine-buying benefit that works best for you.
More Time. More Wine. More to Discover.
We know our guests' expectations have evolved. This year's VIP experience is designed to give you more time, a broader selection of wines and more opportunities to learn directly through tasting and discovery.
Whether you're joining us for the first time or returning for another WineFest weekend, we look forward to welcoming you back to St. Michaels for two days of great wine, discovery and community.
You Should Know
Alcohol must remain inside festival venues. Maryland state law does not permit alcohol outside designated venues. Before leaving a venue, you will be asked to finish or dispose of any remaining wine.
Water stations are available. Complimentary water stations will be available at each WineFest venue throughout the weekend.
WineFest is a 21+ event. All guests must be 21 or older. Children and pets are not permitted.
Festival parking is available at St. Michaels Elementary School.
200 Seymour Avenue
St. Michaels, MD 21663
Refund Policy: WineFest is a rain or shine event. No refunds will be given.