Destination Downtown Waynesboro (DDW) is the nonprofit organization that promotes and supports downtown businesses and events.
Interested in volunteering for Winterfest? Sign up HERE!
Winterfest, Saturday, November 28, 2026
Come to Downtown Waynesboro for Small Business Saturday and to kick off the Holiday season! It’s the most wonderful time of the year! We’ll have activities for all ages, all day long! More details to come, but your favorites will be back and we’ll have new activities as well! 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 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!
Caroling with Main Street United Methodist Church: 11-1:00 pm, Downtown
Kids Holiday Craft at Shelf Indulgence: 11-4:00 pm, 108 S Wayne Avenue
DIY Pinecone Birdfeeders, Activity for Kids at the Heritage Museum: 11-4:00 pm, 420 W Main Street
AND WE HAVE MORE COMING!
Thank you to our sponsor:
Hiker Fest 26, June 6, 2026
June 6, 2026 | N Wayne Ave | Downtown Waynesboro, VA | 11 am – 8 pm
Welcome to Hiker Fest, the ultimate celebration of outdoor adventure in the heart of Waynesboro, VA! Get ready for a day of live music, free yoga sessions, henna designs, local food, trail talks, DIY tie dye, tarot reading, outdoor vendors showcasing their wares, and more! Hiker Fest definitely has something for everyone. We also offer exclusive discounts for AT thru hikers and a complimentary breakfast for anyone with their AT hangtag. Join us as we come together to celebrate nature, music, and the joy of exploration at Hiker Fest! Admission is FREE! Bring your 2026 thru hangtag for free breakfast and deals from vendors!
Free breakfast for hikers at the Russell Museum 9 – 11:00 a.m. Two free yoga practices throughout the day.
Hiker Fest Kick Off Party Friday, June 5, 2026
AT Thru Hikers! This is for you! Start the Hiker Fest weekend off with some Trail Magic at Rockfish Gap when you hop off the trail. Appalachian Long Distance Hikers Association and Waynesboro Tourism will be hosting a hiker feed sponsored by McKee Foods from 8:00 am until 4:00 pm. We’ll also be running shuttles down the mountain and into Waynesboro all day. Hikers can also enjoy free camping downtown. Stop by the YMCA (648 S Wayne), Waynesboro Public Library (600 S Wayne), or Waynesboro Visitors Center (301 W Main) to get your free two night camping pass.
Hiker Fest Saturday, June 6, 2026 | 11am-8pm
Schedule of events and activities
At The Russell Museum:
Free Breakfast for Hikers 9am-11am at the Russell Museum
Hiker Talks Schedule at The Russell Museum
10:00 am – 11:00 am: Trail Maintenance
11:00 am – 12:oo pm: Warren Doyle
12:00 pm – 1:00 pm: Not Oatmeal (at Stone Soup Books)
1:00 pm – 2:00 pm: Ms. Janet, Trail Angels
2:00 pm – 3:00 pm: Gary Windham, 2193 miles
3:00 pm – 4:00 pm: Warren Doyle
Free Yoga Practice 11:00 am and 3:00 pm
At Stone Soup Books:
2:00 pm – 3:00 pm: Storytime with Not Oatmeal
Outdoor and local artisan vendors, N Wayne Ave, 11am-6pm
Food at the Festival by Delly Up, N Wayne Ave, 11am-8pm
Basic City Beer, N Wayne Ave, 11am-8pm
Live Music Lineup | Stage at N Wayne Ave and Main St
11:00 am – 1:30 pm – Hot Mamas
2-4:30 pm – Andy Tichenor’s Almost Acoustic
5-8:00 pm – Nightfall of Diamonds
Vendors
Destination Downtown Waynesboro
Appalachian Long Distance Hikers Association
Raggle Taggle Market
South River Watershed Coalition
Tattoo Mountain
Blanc Creatives
Face painting with Victoria
Life Off the Rocks
Ms. Janet Photography
Potomac Appalachian trail Club
Old Dominion Appalachian Trail Club
Sol Focus Running
Blue Ridge Bud Co.
Rawley Mountain Supply
Thank you to our Hiker Fest 2026 Sponsors! We couldn’t do this without you!
If you’re interested in sponsoring Hiker Fest or would like to be a vendor or volunteer, please shoot us an message!
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. 325 W Main 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
Waynesboro’s only children’s museum. Located in downtown, children learn through play and exploration in environments designed just for them. 201 Short Street, closed Friday, Sunday, Monday
Blue Ridge Children’s Museum’s Natural playground is where children can play and enjoy nature simultaneously. 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!
