Holiday Sip & Stroll | Waynesboro

Saturday December 12th, 2026 * 1:00 PM – 4:00 PM Our most beloved Sip & Stroll is back! Get into the holiday spirit with an afternoon of festive fun, local flavors, and downtown cheer! Pick up your Sip & Stroll passport at 66 West Main Street, then make your way through downtown Waynesboro, visiting participating local businesses along the way. Enjoy samples of local beer, wine, and spirits while discovering all that our downtown has to offer. Break out your most outrageous, festive, or downright ugly Christmas sweater for our Ugly Christmas Sweater Contest at 4:00 PM! Prizes will be awarded, so come dressed to impress (or maybe not impress)! Gather your friends, embrace the holiday spirit, and join us for some festive sipping, strolling, shopping, and supporting local businesses! Must be 21 years of age or older to participate. Valid ID required at check-in. GET YOUR TICKETS HERE! https://www.eventbrite.com/…/holiday-sip-stroll-tickets…