04/30/2026
🍷🎉 Come sip with us in the Coolest, Best, and now greatest Main Street in America!
Dive into a day full of flavor and fun in historic Sykesville, a proud Great American Main Street Award (GAMSA) winner. Enjoy UNLIMITED wine tastings featuring the best of Maryland alongside international favorites from Sonoma, Argentina, France, and Italy. All served in your collectible Sykesville wine glass. Enjoy live entertainment, local artists, delicious food, and the vibrant charm of our small-town business community. It’s an unforgettable celebration of wine, culture, and community! 🥂✨
https://tickets.downtownsykesville.com/
🎉 May 2, 2026, is going to be unforgettable!
Join us for the Downtown Sykesville Art & Wine Festival, where incredible flavors, great company, and small-town charm come together for one amazing day.
🍷 Sip your way through exquisite wines from top Maryland wineries and international favorites
🍴 Enjoy delicious bites from beloved local eateries
🎨 Explore local artists and soak in live entertainment all day long
🎶 Rock out with the Garrett Mabe Band, Enslow, and discover unique experiences like plein air painting, flash tattoos, live alpacas, and more—there’s truly something for everyone!
🚌 Getting here is easy with exclusive ticket-holder shuttles running from Sykesville Middle School and Freedom Park, plus ADA-accessible transportation, restrooms, and a sign language interpreter for live performances—so everyone can join in the fun.
🎟️ Check-in is quick and simple—just bring your ID and we’ll handle the rest.
💖 Every ticket supports the Downtown Sykesville Connection and helps us continue building a vibrant, thriving Main Street community.
https://tickets.downtownsykesville.com/