Destination Downtown Waynesboro (DDW) is the nonprofit organization that promotes and supports downtown businesses and events.
Events
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-along 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-along fun! Cocoa provided by Kline’s Espresso Bar. Cookies provided by Bonobos Bakery.
Bring your camera, your holiday spirit, and your biggest smiles!
One free adult ticket is included with each child’s ticket! Get your tickets here!
11 am – 4 pm: Cookie Trail, Various Businesses **This event is 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 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+.
11am – 4 pm: Face Painting with The Glitter Bee at The Russell Museum
Get your face painted while you enjoy the fun
11 am – 1 pm: Meet Santa at The Russell Museum
Bring your kids, your pets, your significant other, or anyone else, 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!
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.
11 am – 4 pm: Snowflake Craft and Marshmallow Sensory Activity
Blue Ridge Children’s Museum will be set up in Bruce Alley with Parks and Rec doing some fun winter themed crafts! Donations will support the Blue Ridge Children’s Museum’s new indoor space at 201 Short Street!
12 pm – 4 pm: Meet the Grinch
Find the Grinch in Downtown Waynesboro for a meet and greet and some photos!
1 pm – 2 pm: Story Time with Santa at Stone Soup Books
Join Santa at Stone Soup Books as he reads a special Holiday story!
2 pm – 4 pm: Holiday Concert at The Russell Museum. Sponsored by Rusticae.
Get ready to rock around the Christmas Tree at the Russell Museum for a FREE Holiday Concert with Heidi Hill!
All Day Activities
Purchase a limited edition Waynesboro Christmas Ornament for just $10 at the DDW Info Booth. Sponsored by Initial Inspiration.
Window Decoration Contest
Vote for your favorite Holiday themed window!
Inflatable Snow Globe Photos and the DDW Information Booth
Climb into 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!
DIY Holiday Hat Bar at Initial Inspiration
Decorate a hat for you or as a holiday gift at Initial Inspiration! Take it to adorn. for free gift wrapping!
Wine Tasting Room OPEN at Lightwell Survey
Lightwell Survey’s tasting room will be open from 12-5:00 pm in the South River Mill, 200 W 12th Street, Unit D53. If you haven’t tried them yet, this is the last Saturday their tasting room will be open for the season. Stop by to warm up after Winterfest!
Check back soon! We’re adding more everyday!
Virginia Street Arts Festival – May 16-17, 2026
Details coming soon!
Where to Eat
Downtown Waynesboro has a diverse and gratifying dining scene, try all of our local restaurants!
Royal India Palace
Authentic Indian cuisine in a upscale atmosphere. Perfect for lunch, dinner, or carryout. 309 W Main Street, closed Tuesday
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
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
Kline’s Espresso Bar
Drive thru coffee bar featuring craft lattes and specialty drinks. 1234 W Broad 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. 317 W Main Street, 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
Stone Soup Books at the South River
Community bookseller and book rescuer. 402 W Main Street, open Wednesday-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
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, closed Sunday-Wednesday
Augusta County Railroad Museum
Enjoy railroad displays and layouts in this FREE museum. 413 W Main Street, open Saturdays, 1-4pm (visit AACRM.com for additional hours)
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.
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.
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!
