Cookie Trail: 11-4 pm, Downtown **SOLD OUT**
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 28 starting at 11 am at the DDW Info Booth, 503 W Main Street. Stroll around Downtown Waynesboro and pick up individually wrapped holiday cookies at 13 different businesses while you shop, sip, and dine and end up with a baker’s dozen of delicious, decorated winter cookies! 
Participating businesses:
Boutique in the Boro, adorn., Rusticae, Augusta County Rail Road Museum, Shenandoah Valley Art Center (South Wayne Ave), The Russell Museum, The French Press, Initial Inspiration, Stone Soup Books, Shelf Indulgence, Crack O’ Dawn, Waynesboro Watershed Coalition, and more!
Wassail Trail: 11-5 pm, Downtown
Delly Up (Undefeated champion!), Benny Stivale’s, Royal India Palace, The French Press, The Russell Museum, Pyramid, Stone Soup Books, Initial Inspiration, Rusticae, Farmers Market Winterfest Market, and more!
Cocoa and Cookies with the Princesses: 10-11 am, 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 winter magic crown and wand. Don’t miss the sing-a-long with the princesses before they head off to spread more cheer downtown! When: November 28 from 10-11:00 am — one hour before Winterfest!
Where: The Russell Museum, Downtown Waynesboro
Includes: Cookies, cocoa, winter magic crown and wand, and sing-a-long fun! Bring your camera, your holiday spirit, and your biggest smiles!
Tickets are $25 per child and includes one adult.
Photography Release: By purchasing a ticket to this event, you consent to Destination Downtown Waynesboro (DDW) and Character Connections photographing you and/or your child and using those images for promotional and marketing purposes, including social media, websites, and printed materials. Photos will not be used for AI-generated content or AI image manipulation.
NEW Trot and Toddy Fun Run or Walk: 10:30-11:00 am at Constitution Park Pavilion
Join us downtown for a holiday fun run/walk that’s open to all ages and pay what you will! It’s ¾ of a mile out and ¾ of a mile back, for a grand total of 1.5 miles. That’s roughly half a 5K, so no need to train, just bring your friends and enjoy a morning walk or run on the Greenway. All participants receive a Santa hat, participants 21+ get a Wassail Trail passport and those under 21 will get a Kids Wassail passport!
Dress up as Santa, your favorite character from ‘The Grinch’, or whatever gets you in the holiday spirit so you can enjoy a full day of activities at Winterfest! So, register now to run, walk, or jog for a fun way to kick off the holiday season.
Never wassailed before? Wassail is a traditional holiday drink, typically made with warm spiced cider, and wassailing is the centuries-old tradition of gathering, drinking, and spreading good cheer. So, after the run, keep the festivities going with the Winterfest Wassail Trail, featuring alcoholic and nonalcoholic holiday drinks at participating downtown businesses. Thanks to Destination Downtown Waynesboro’s designated outdoor refreshment area (DORA), you can enjoy your drinks while strolling through downtown. Grab your friends, do a little holiday shopping, and make a festive bar crawl out of it! Registration is required, so sign up now!
Meet Santa: 11-1pm at The Russell Museum and 1:30-2:15 pm at Stone Soup Books
Meet Santa at The Russell Museum from 11am – 1pm and take some photos with your kids, your pups, or both!
Spend story time with Santa at Stone Soup books from 1:30pm – 2:15pm! These events are FREE!
DIY S’mores: 11-4 pm in Bruce Alley
Join Waynesboro’s Parks and Rec as they haul out the fire pits and bring all the fixings for DIY s’mores! This activity is free!
**This event is NOT in Lumos Plaza, it is in Bruce Alley, beside the P Buckley Moss Gallery next to Main Street**
NEW Farmers Holiday Market: 11-4:00 pm at 522 W Main Street, right beside The Russell Museum
Come see some of your favorites and some new artisan vendors at the Waynesboro Farmers Market’s Holiday Market! Bring the kids for a reindeer food activity! Interested in vending? Email markets@projectgrows.org for an application!
NEW Holiday Dog Portraits: 11-4:00 pm, 417 W Main Street
Details coming soon!
NEW Tree Lighting with Waynesboro Parks and Recreation: 5:30 pm, Constitution Park
What says Christmas more than gathering around a tree and watching it light up? Join Waynesboro Parks and Recreation for an old-fashioned tree lighting in Constitution Park and help us wrap up Winterfest with a little holiday magic!
Snow and Giant Snow Globe: All day long at City Hall!
Even if it’s not snowing, you can pretend at City Hall! Listen to Christmas music with the snow coming down and take a pic and have some fun in a giant snow globe/bounce house! Suggested donation of $2 for snow globe photos!
DIY Ornament Station with Office on Youth: 11-4:00 pm, Bruce Alley
Make your own ornament or take it with you to make at home!
Face Painting with Glitter Bee: 11-4:00 pm, location TBD
Come see the Glitter Bee for face painting during Winterfest!
FREE Gift Wrapping at adorn.: 11-4:00 pm at adorn., 141 N Wayne Avenue
Bring your purchase from any downtown business to adorn. with a receipt from Winterfest, November 28th and have it beautifully gift wrapped for free!
