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



Tour the Town

Join us in Downtown Waynesboro for the third annual Tour the Town on Wednesday, May 29, 2024 from 12-8:00 p.m.! Get your passport and eat, drink, and play your way through Downtown. This passport will get you access to exclusive deals in our boutiques, food and drink samples at local eateries, and other fun things like a mini henna tattoo and a beautiful Waynesboro art print! Bring the kids along for their own scavenger hunt to earn a free glitter tattoo and ice cream cone coupon! Round out your day with the Wayne on Main concert on under the Wayne Theatre’s marquee and a drawing for Waynesboro swag. Check back often, we’re adding more participants all the time!
Get your passport now!

Benny Stivale’s

Half a slice of their famous giant slice and a beer sample

Delly Up

Hoagie quarter and beer sample

The Glitter Bee

Free mini henna tattoo
Free mini glitter tattoo as scavenger hunt prize for kids accompanying a participating adult

Stone Soup Books at the South River

$5 Gift Card


Free lip gloss OR facemask with any purchase

Boutique in the Boro

10% off the store

The French Press

Free small beverage of your choice

Shenandoah Valley Arts Center



10% off the store

Initial Inspiration

$10 Gift Card with any purchase

Waynesboro Farmers Market

Free tote bagvoucher redeemable at the Farmers Market on Saturdays at Constitution Park

Waynesboro Heritage Museum

10% off in the gift shop or a beautiful Waynesboro art print

The Russell Museum

$15 Gift Card to the bookstore and free self guided tour

The River Burger Bar

Skipping stones and beer tasting

Pyramid Appalachian Magick + Remedy

Free bag of tumbled stones with any purchase

The Wayne Theatre

Free popcorn at the Wayne on Main concert

The Gumbo Hut

Free sample of the Gumbo Hut’s famous gumbo!

Kline’s Dairy Bar

Free cone gift card and free kid’s cone card gift card for kids accompanying a participating adult

C C Soul Bistro

Pulled pork BBQ slider

Sams Hot Dog Stand Waynesboro

One of Sam’s famous hot dogs

Lukes Hobbies LLC


Hiker Fest 2024

June 8, 2024 in Downtown Waynesboro. Check out our Hiker Fest page for more info.

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

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 womens 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


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 featurestwo 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

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!