Destination Downtown Waynesboro (DDW) is the nonprofit organization that promotes and supports downtown businesses and events.
Events
WAYNESBORO WINTERFEST
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
Special Thanks to Jeff Fife, Agent with Westhills Realtors
Where to Eat
Downtown Waynesboro has a diverse and gratifying dining scene, try all of our local restaurants!
The River Burger Bar
Features awesome burgers and a variety of vegetarian, vegan, and gluten free options.137 N Wayne Avenue, closed Wednesday
Sam’s Hot Dog Stand
Virginia’s best hot dog stand featuring famous chili sauce and pork BBQ sandwiches.416 1/2 W Main Street, closed Sunday
C.C. Soul Bistro
Sandwiches, and local artisan goods.414 W Main Street, closed Sunday-Monday
Delly Up
Sandwich and drink shop serving up great food and local beer, wine, and cider for dine-in or take-out.421 W Main Street, closed Tuesday
Stella, Bella, Lucy’s
Excellent option for breakfast and lunch featuring a fresh, flavorful menu.327 W Main Street, closed Sunday-Monday
Benny Stivale’s
Stop in for a fresh slice or a gigantic 28″ pizza. Home to Waynesboro’s secret beer garden.328 W Main Street
The French Press
Gourmet coffee, pastries, and homemade paninis all served in a cozy, quaint atmosphere.134 N Wayne Avenue, open daily
The Gumbo Hut
Authentic Cajun and Creole gumbo, étouffée, and more. Dinner only.403 W Main Street, closed Sunday-Wednesday
The Green Leaf Grill
Weekly specials, fresh seafood, a wide variety of vegetarian options, and craft cocktails. Dinner only.415 W Main Street, closed Sunday-Monday
Crack O’ Dawn
Dedicated gluten free bakery and bistro that specializes in breakfast and lunch.908 W Main Street, closed Wednesday
Kline’s Dairy Bar
Sweet treats including ice cream, sundaes, milkshakes, and more.1235 W Main Street, open daily
Where to Shop
Waynesboro has plenty of unique shops located right Downtown
South River Fly Shop
Full-service fly fishing shop and guide service.309 W Main Street, open daily
adorn.
Upscale boutique specializing in women’s clothes and accessories.141 N Wayne Avenue, closed Sunday-Monday *Check link for Holiday hours
Luke’s Hobbies
R/C, scale model, slot car, paint, accessories, on-site dragstrip and more!400 W Main Street, closed Sunday-Monday
Alpha and Omega Antique Mall
Antique shop offering a variety of vintage treasures.232 Arch Avenue, open daily
Initial Inspiration
Gift shop featuring embroidery, monograms, and personalized jewelry.412 W Main Street, closed Sunday-Monday
Pyramid: Appalachian Magick + Remedy
Unique shopping experience with everything from handcrafted incense to loose herbs and teas.139 N Wayne Avenue, closed Monday
Boutique in the Boro
Boutique offering a wide array of women’s fashion and accessories including Judy Blue jeans.108 S Wayne Avenue, closed Sunday-Monday
Under the Roof
High quality furniture store carrying the best brands and offering free design consultations.406 W Main Street, closed Sunday-Monday
Waynesboro Florist
Florist and gift shop offering delivery.325 W Main Street, closed Sunday
Stone Soup Books at the South River
Community bookseller and book rescue on the banks of the South River.150 Race Avenue, open Thursday-Sunday
Waynesboro Music
Full service instrument store featuring lessons, setup, and jam sessions.520 W Broad Street, closed Sunday-Monday
Cross Stitch Station
Cute shop with plenty of cross stitch supplies and home goods.520 W Broad Street, closed Sunday Monday
Rusticae
Vintage and new home décor and fashionable attire.326 W Main Street, closed Sunday Monday
Healthy Habits
Vitamin supplement shop empowering healthier lives.510 B W Broad Street, closed Sunday-Monday
Museums
Explore Waynesboro’s rich history and amazing art at one of Waynesboro’s museums
Waynesboro Heritage Museum
Learn the history of Waynesboro through permanent and revolving exhibits. Donations welcome. 420 W Main Street, closed Sunday-Monday
The Plumb House Museum
Visit the oldest frame structure in Waynesboro and part of the Civil War’s Battle of Waynesboro.1012 W Main Street, by appointment 540-943-3943
The Russell Museum
Experience the artwork of Walter Russell through both painting and sculpture.518 W Main Street, open house 2nd Saturday of the month, call 1-800-882-LOVE to schedule a tour
Blue Ridge Children’s Museum and Natural Playground
Natural playground where children can play and enjoy nature simultaneously.201 Short Street, open daily from dawn to dusk
The Arts
Waynesboro has a vibrant arts scene! Check out all we have to offer:
Shenandoah Valley Art Center
A place to look at, learn about, and talk about ART! Gallery, gift shop, and working artists.122 S Wayne Avenue and 416 W Main Street, closed Sunday-Monday. *Discover quality handmade gifts at the Winter Market now through January 13th at both locations
Wayne Theatre and Performing Arts Center and Exhibit Hall
Waynesboro’s premier performance venue and exhibit hall.521 W Main Street, visit WayneTheatre.org for a full schedule of events. *Live performances of ELF begin
P Buckley Moss Gallery
Come see the work of famed artist P. Buckley Moss in this downtown Gallery.329 W Main Street, closed Monday
Trails
This City loves trails! Downtown features two unique trails for you to explore.
Street Arts Trail
One-of-a-kind mural trail with almost two dozen stops featuring eye-catching art and murals. Downtown Waynesboro and beyond, stop by 301 W Main for a rack card, or go to WaynesboroStreetArtsTrail.com for a fun scavenger hunt style tour and more information about the art installations.
Waynesboro Water Trail
Four miles of scenic river perfect for all levels of paddlers winding right through downtown Waynesboro. Click the link for map of put-ins and let-outs.
Green Spaces
The South River Greenway
Constitution Park
DORA: Waynesboro is a DORA community
DORA stands for Designated Outdoor Refreshment Area and allows visitors to downtown Waynesboro to take their drinks while shopping and enjoying downtown art and museums during designated DORA events. Look for the boundary signs and read over the ABC guidelines. And be sure to have fun!
