Get ready to kick off the holiday season with a brand-new celebration in Downtown Waynesboro! Winterfest is here to bring Small Business Saturday to life on November 30, from 10 am to 6 pm. Spend the day with us shopping local, enjoying festive activities, and soaking up holiday cheer all across Downtown. From family fun to one-of-a-kind shopping, we’ve got everything you need to jump-start your season with style. Check out all the fun Winterfest has in store for you and the whole crew!
**SOLD OUT** Cookie Trail – Get your tickets here!, 11-4 pm*
Get your ticket and go on the Winterfest Cookie Trail!
Hop on the Winterfest Cookie Trail and satisfy your sweet tooth while exploring downtown! For $15, you’ll receive a Winterfest Cookie Trail bag and passport, guiding you to 13 local businesses where delicious holiday cookies await. Collect treats, support small businesses, and enjoy festive activities as you enjoy the festively decorated Downtown. Perfect for families, friends, or anyone craving a taste of holiday cheer, this trail is a must-do at Winterfest! Participating businesses where you get your cookie: Boutique in the Boro, Freda’s Skin Studio, The French Press, P Buckley Moss Gallery, Shenandoah Valley Art Center (416 W Main), Augusta County Rail Road Museum, The Russell Museum, adorn., Initial Inspiration, Waynesboro Music, Luke’s Hobbies, Rusticae, and Pyramid
Wassailing Trail, 11-6 pm
Stroll along the Wassailing Trail at Winterfest and sip festive holiday drinks from your favorite downtown restaurants! Grab a passport 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 sip 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! This trail contains alcoholic and non-alcoholic drinks, must be 21+ to participate. Participating businesses where you can grab your drink: The River, Delly Up, The Russell Museum, The French Press, Benny’s
Raffle for ‘A Christmas Story’ Mini Leg Lamp, ALL DAY*
$5 per raffle ticket, 5 for $20! Get your tickets at 503 W Main Street all day! The winner will be contacted Monday, December 2nd.
Downtown BINGO, ALL DAY
Get a BINGO while you’re wassailing and shopping and be entered for awesome prizes like a Baggallini weekender bag from adorn.! Get your FREE BINGO card from 10 am – 5 pm at our booth at 503 W Main Street.
Elf Door Scavenger Hunt, ALL DAY
Grab the kids and find 10 miniature elf doors scattered around downtown! Find them all and get some Waynesboro swag. Get all the details at our booth at 503 W Main Street.
Pictures with Santa, 11-3 pm
Come to The Russell Museum to visit with Santa and take pictures!
Meet and Greet with the Grinch, 11-4 pm
Find the Grinch Downtown from 11-4 pm for a meet and greet and pictures!
Face Painting with the Glitter Bee, ALL DAY*
Rusticae will be hosting the Glitter Bee for Winterfest! The Glitter Bee will be offering face painting, henna, glitter tattoos, and sparkle hair (by appointment)!
Caricature Portraits, ALL DAY*
Get your funny portrait made at The Russell Museum!
Meet and Greet with the Grinch, 11-4 pm
Find the Grinch Downtown for a meet and greet and photo opportunities!
Window Decorating Contest, November 30 – December 8
As you’re strolling Downtown collecting cookies, having a cup of holiday cheer, getting BINGO… however you’re celebrating Winterfest, be sure to take a look at all the beautifully decorated windows. You can vote for your favorite by scanning the QR code on the window. The winning window will get a *Major Award*, a full sized leg lamp from ‘A Christmas Story’ that they can show off until next year!
Christmas Music Concert with Matt Johnson, 2-4 pm
Enjoy an intimate Holiday concert with Matt Johnson from The Voice at Main Street United Methodist Church. Sponsored by Rusticae and Main Street United Methodist Church.
Pet Photos, 10-2 pm
Get your pets Holiday photo taken at Initial Inspiration! You can have it put on an ornament too!
Gift Wrapping Station, 12-5 pm
Bring your purchase from a Downtown business to adorn. with a receipt from November 30th and have it gift wrapped!
Photo Ops
Grab a picture with Santa at The Russell Museum (times, TBA), the Grinch (12-4 pm at various locations downtown), IN a giant inflatable snow (all day outside of City Hall), with a historic Model A car (all day beside The Russell Museum), and we’ll have SNOW at our booth outside of City Hall all day too!
Holiday Pottery Sale 10-5 pm
Make Waynesboro is having a huge pottery sale at Shenandoah Valley Art Center (416 W Main St) from November 4 – December 28. Cross some gifts off your list!
Carolers Every Hour from 11-3 pm
Enjoy a caroling station with local musical community choirs on Stone Soup Book’s loading dock on the hour from 11-3 pm. They will also be serving Saturday Sweets & Treats with traditional Meriwether Fruitcake and spice cookies. Come enjoy some sweets and songs!
*Activities that have a cost or ticket associated with them
