Waynesboro Winterfest
Schedule
Sat Nov 29 2025 at 11:00 am to 05:00 pm
UTC-05:00Location
Waynesboro, VA - City Hall | Waynesboro, VA
Advertisement
Come to Downtown Waynesboro for Small Business Saturday and to kick off the Holiday season! We'll have activities for all ages, all day long!❄️Cookies and Cocoa with the Princesses, 10 am - 11 am at the Russell Museum: Get ready for a royal holiday treat! ✨
Meet your favorite winter princesses at the Russell Museum one hour before the Winterfest festivities begin. Little princes and princesses can sip hot cocoa, have some cookies, and enjoy songs straight from the castle. Each child will receive a special autograph card to collect signatures from the princesses and take home a magical keepsake. Don’t miss the sing-a-long with the princesses before they head off to spread more cheer downtown! One free adult per child's ticket. Get your tickets now!
❄️Cookie Trail, 11 am - 4 pm: Kick off the holiday season with the Winterfest Cookie Trail! Get your ticket now (limited tickets available) and pick up your Winterfest Cookie Trail bag on November 29 starting at 11 am at 503 W Main Street. Stroll around Downtown Waynesboro and pick up individually wrapped specialty holiday cookies at 13 different businesses while you shop, sip, and dine and end up with a baker's dozen of delicious, decorated cookies! Pick up your cookie bag at 503 W Main Street! Limited tickets available.
❄️Wassailing Trail, 11 am - 4 pm: Stroll along the Wassailing Trail at Winterfest and sip festive holiday drinks from your favorite downtown restaurants and shops! Grab a passport for just $5 from our booth at 503 W Main Street and sip, shop, and dine to get in the holiday spirit. Cast your vote for the best seasonal drink after you’ve tried them all. The winning establishment will earn the coveted Holiday Cheermeister award, along with a full year of well-deserved bragging rights! Tickets can be purchased at our info booth or added on when you get your Cookie Trail tickets! This is a DORA event! Grab your favorite drink and take it shopping with you!
❄️Pictures with Santa, 11 am - 2 pm at Stone Soup Books: Bring your kids, your pets, your significant, or whoever you want and meet and greet with Santa while you get some pics!
❄️Elf Door Scavenger Hunt, 11 am - 5 pm: Pick up the elf door scavenger hunt instructions at the DDW info booth. Find them all and get a prize from Kline’s Dairy bar!
❄️Raffle for 'A Christmas Story' leg lamp
❄️Free Giftwrapping for downtown purchases at adorn.
❄️Winter Market at Shenandoah Valley Art Center
❄️Carolers from Main Street United Methodist
❄️Caricature artist at the Russell Museum
❄️Holiday Concert with Matt Johnson: Details coming soon!
❄️Giant Snow Globe photo opp
❄️Find the Grinch
❄️And More!
Check back for more details coming soon!
*This is not a vendor event*
Advertisement
Where is it happening?
Waynesboro, VA - City Hall, United StatesEvent Location & Nearby Stays:
Know what’s Happening Next — before everyone else does.
