After 17 amazing years, Winefest at St. Michaels is getting a whole new VIP experience—and we think 2027 will be our best Winefest yet!

Get ready for a weekend filled with exceptional wine, great friends and unforgettable moments in the beautiful setting of St. Michaels.

Whether you’re a wine enthusiast looking or new to the glass, WineFest is for you with something for everyone!

We recommend VIP options to make the most of the weekend and receive special perks!

NEW FOR 2027: ALL TICKET BUYERS WILL RECEIVE A LANYARD WITH THEIR MAP & GLASS!

Important Info:

Ticket tents will be open to process and sell tickets early each day (10 am on Saturday and 10 am on Sunday). Venues will open at 11am and close at 5pm each day.

This is a walkable event in downtown St. Michaels - however all glasses must be empty when leaving a venue! Open-containers are not allowed per law!

All attendees must stop at one of the ticket tents to get their ID checked.

Children, pets and strollers are not permitted for this 21+ event.. NO EXCEPTIONS.  

Designated Driver:  All visitors are welcome to visit the outside vendors who have come to our event to show off their various products and services.  WineFest bracelets are required only for the wine tasting tables.  A bracelet is not required if you are not tasting/

Map: You will be provided a map with you check in at the ticket booth for your ID check and glass! All venues, restrooms and water stations are clearly marked on the WineFest map .

Parking: Plan to park your car at the St Michaels Elementary School unless you're staying in town. Downtown parking is limited. 

*** A NEW VIP EXPERIENCE FOR 2027 ***

For 2027, we are introducing TWO VIP TICKET OPTIONS, making the VIP experience accessible to wine lovers with different budgets.

VIP guests will enjoy dedicated VIP tastings on BOTH days, with the opportunity to visit two exclusive VIP locations, each featuring 20+ exceptional wines.

The new format gives you 2+ hours of VIP tasting each day at a relaxed pace, with plenty of time to explore the other Winefest venues, stroll through St. Michaels, and enjoy everything the weekend has to offer.

VIP wines will be available for purchase at special prices, and discount coupons are included with both VIP ticket options.