Destination Downtown Waynesboro

November 17, 2023
Arts & Culture, Food, Craft Beverage, History

Destination Downtown Waynesboro (DDW) is the nonprofit organization that promotes and supports downtown businesses and events.

Explore Downtown Waynesboro





Small Business Saturday and Bingo

November 25 | 11:00 pm - 6:00 pm | Downtown Waynesboro | Paticipating Merchants

Start your weekend and the beginning of the holiday shopping season off right with an interactive game of scavenger hunt bingo!

  • Grab your friends and family, head downtown, and pick up a Bingo card from a participating business (adorn., Magnolia Rose, Delly Up, Pyramid, The City Foxes, Initial Inspiration, Boutique in the Boro, Rusticae, Waynesboro Heritage Museum, Waynesboro Music, Shenandoah Valley Art Center, Sam's Hotdogs, The Russell Museum, and The River Burger Bar).
  • On the Bingo card there will be a mix of restaurants, retailers, and landmarks. Visit the downtown merchants to get your card stamped and identify the landmarks to get five squares in a row - vertical, horizontal, or diagonal - for BINGO!
  • Turn in your card at the Russell Museum for a grand prize drawings of Downtown business' gift cards, merchandise, and Waynesboro swag (you DO NOT have to be present to win, winners will be announced Monday, November 27th). Everyone that participates will get an 'I Heart the Boro' button when you turn in you card at the Russell Museum.

????This is a DORA event! Grab a drink from a downtown restaurant and take it with you while you play Bingo! Keep an eye out for retailers that have green DORA stickers (you can take your drink in) and boundary signs and rules.

We have tons of prizes including adorn beauty bag, $25 gift card to Boutique in the Boro, $25 gift card to Delly Up, $25 gift card to Pyramid, Kline's free ice cream card and logo t-shirt, Waynesboro swag, and more!


Participating Businesses:


Delly Up

Magnolia Rose


Luke's Hobbies

The City Foxes

Initial Inspiration

Boutique in the Boro


Waynesboro Heritage Museum

The Gumbo Hut (Opens at 2:00 pm)

Waynesboro Music (Closes at 4:00 pm)

Shenandoah Valley Art Center (Closes at 4:00 pm)

The Russell Museum (Bingo card drop-off location)

Sam's Hotdogs

The River Burger Bar

Stone Soup Books

Holiday Market

December 2 | 10:00 am - 4:30 pm | Lumos Plaza and Bruce Alley

Head downtown to kick off the holiday season! Vendors, Santa, hot chocolate, and more! Don't forget to walk around downtown and vote for your favorite decorated window! The winning window merchant will recieve a MAJOR AWARD, a life size leg lamp from the movie, A Christmas Story. Find the lamp during your stroll and win a Waynesboro logo prize!

Vendors include:

Backpocket Provisions

Glitter Bee facepainting and henna

Lucky Duck Kettle Corn

Twisted Roots

Wooden Bouquets

Valley Scent


Luke's Lures

Lima Designs

The Freckled Tulip

Lusca Creatives

Stephanie Rose Crochet and more

High & Low Macrame


MH Designs

Murphy Makery

Dawn Toler Crafts

The Wander Studio

Dandy Dyes Design Co.

Diana's Adorable Bears

Better Carob

and MORE!!

This is a DORA event! Grab a drink from a downtown restaurant and take it with you while you play Bingo! Keep an eye out for retailers that have green DORA stickers (you can take your drink in) and boundary signs and rules.


L.L. Bean Pop-Up Shop and VMNH Mobile Exhibit Grand Opening

Come to Constitution Park December 9th and 10th to shop L.L. Bean's pop-up shop and Bootmobile! Find all your LL Bean favorites and discover new ones right in downtown Waynesboro! 

The Virginia Museum of Natural History will also be hosting the grand opening of their mobile exhibit trailer which will be permanently placed in the park until the museum groundbreaking. Stop by after shopping and get a sneak peek of what's to come in Constitution Park!

As an added bonus Cousins Maine Lobster will  be there Sunday, December 10th. If you haven't tried their fresh lobster, it's a must! It's a match made in Maine Heaven!



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!


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

The City Foxes Wine Bar + Market

Virginia wine, fresh 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

Heritage on Main

A contemporary menu with something for everyone and a fine dining flair. 309 W Main Street, closed Monday

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


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

Tubular Toy Box

Vintage toy shop with nostalgic finds, comics, and collectibles. 130 N Wayne Avenue, open Friday-Sunday

Pyramid: Appalachian Magick + Remedy

Unique shopping experience with everything from handcrafted incense to loose herbs and teas. 139 N Wayne Avenue, closed Monday

Magnolia Rose

Shop a curated group of diverse pop-up vendors and support a great cause. 417 W Main Street, closed Sunday-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


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







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 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





This City loves trails! Downtown features two unique trails for you to explore.

Street Arts Trail

One-of-a-kind meral 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 download the free Traipse app for a fun scavenger hunt style tour. 

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







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