Winterfest/Small Business Saturday – November 29
Kick off the holiday season in Downtown Waynesboro on Saturday, November 29 from 11 am – 5 pm during Winterfest, a full day of festive fun celebrating Small Business Saturday. Bring the whole family, support local businesses, and make a day of it in Downtown!
Schedule of Events:
10 am – 11 am: Cookies and Cocoa with the Princesses 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!
When: November 29 from 10-11:00 am — one hour before Winterfest
Where: The Russell Museum, Downtown Waynesboro
Includes: Cookies, cocoa, autograph card, and sing-a-long fun!
Bring your camera, your holiday spirit, and your biggest smiles!
One free adult per child’s ticket! Get your tickets here!
11 am – 4 pm: Cookie Trail, Various Businesses
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. Get your tickets here!
11 am – 4 pm: Wassail Trail, Various Businesses
Stroll along the Wassailing Trail at Winterfest and sip festive holiday drinks from eight of 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! This event features alcoholic and non alcoholic beverages. Participants must be 21+.
11 am – 2 pm: Meet Santa at Stone Soup Books
Bring your kids, your pets, your significant other, or anyone and meet Santa and take some pictures! FREE
11 am -4 pm: FREE Caricature Drawings
Join Ryman’s Caricature’s for your FREE caricature during Winterfest! Tips are accepted and appreciated!
2 pm – 4 pm: Holiday Concert with Matt Johnson at The Russell Museum
Get ready to rock around the Christmas Tree at the Russell Museum for a FREE Holiday Concert with Matt Johnson from The Voice!
12 pm – 4 pm: Meet the Grinch
Find the Grinch in Downtown Waynesboro for a meet and greet and some photos!
11 am – 1 pm: Strolling Carolers
Enjoy Carolers from Main Street United Methodist Church in Downtown Waynesboro!
11 am – 4 pm: DIY S’mores
Hang out with Waynesboro Parks and Rec in Bruce Alley (beside P Buckley Moss Gallery) and warm up by the firepit while you make some s’mores! This activity is FREE and all the supplies are provided.
All Day Activities
Purchase a Limited Edition Waynesboro Christmas Ornament for just $10 at the DDW Info Booth
Window Decoration Contest
Vote for your favorite Holiday themed window!
Inflatable Snow Globe Photos and the DDW Information Booth
Climb in the giant snow globe and pose for some Instagram worthy pictures! A $2 donation to the DDW is appreciated!
Elf Door Scavenger Hunt
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!
‘A Christmas Story’ Leg Lamp Raffle
Get your raffle ticket ($5 or 5 for $20) for your chance to win a 26″ deluxe desktop leg lamp, it’s a Major Award!
Find the Snowmen Scavenger Hunt
Download our Waynesboro app and find 10 snowmen hidden virtual reality-style all around downtown! Find them all and get a free coffee token from Kline’s Espresso Bar!
FREE Giftwrapping at adorn.!
Bring your purchase from a Downtown business to adorn. with a receipt from November 29th and have it gift wrapped for free!
Winter Market at Shenandoah Valley Arts Center
Find local, handmade gifts at the Winter Market at SVAC’s Main Street location!
