Ditch the Car and Spend the Weekend in Downtown Waynesboro

May 22, 2023
Stories, Outdoors, Arts & Culture, Food, Craft Beverage, History


Warm weather’s here and it feels great to be outside! Plan a weekend in Waynesboro and spend your time enjoying the outdoors, shopping, dining, browsing museums, and taking in history and the arts…all without having to get in the car.



Friday: Check in at a Cozy B&B or Downtown Motel and Grab some dinner


The Bowman House is a historic 4-room Bed & Breakfast that serves a locally-sourced breakfast and is just four beautiful tree-lined blocks to downtown.

If you want to be budget friendly, Quality Inn has a pool, free breakfast, and free parking and is right around the corner from all the downtown restaurants and shops.



After your trip and check in, you’ll definitely want to grab some delicious food and a cocktail. Head to W Main Street to Heritage on Main for a casual, trendy vibe with a menu full of fresh cuisine and inspired cocktails.

If you don’t feel like dining out, you also can’t go wrong with Cajun takeout from The Gumbo Hut. How does shrimp and crawfish etouffee and a black cherry margarita to take back to your digs sound?



Saturday: Hit the Farmers Market, then spend the day Downtown


Visit the Farmers Market and Shop Downtown

Whether you’re staying at the Bowman House or the Quality Inn, you can take a quick morning walk to pick up a coffee or tea and a breakfast pastry at The French Press or Farmhaus Coffee Co. before heading to the Waynesboro Farmers Market. The Saturday morning market is a wonderful place to mingle with the locals, enjoy the community vibe, talk to farmers, listen to music, purchase fresh fruit and produce as well as local meat and other products.

Waynesboro has lots of cute shops to visit downtown. Locally owned Boutique in the Boro sells women’s fashions and accessories. Find a new-to-you treasure at Alpha and Omega Antique Mall or The Tubular Toy Box. Pyramid: Appalachian Magick + Remedy carries unique items that nurture the mind, body, and spirit and some days you can even get a tarot reading. Initial Inspiration offers trendy apparel and accessories that can be personalized. Magnolia Rose’s pop-up vendors sell locally-made items and benefit a good cause. 

Eat Lunch 

There’s something for everyone at The Mill Yard virtual food hall. Choose from nachos, shareables, or burgers from Hops Kitchen, Detroit-style ZA Spot pizza, savory and creative smoked items from SmokeBox, or the day’s catch from Seafood on Seafood. 

For quick sandwiches and a huge selection of craft beer Delly Up is right on the corner of Wayne and Main and is perfect for people or TV watching.

Tour Downtown Waynesboro

Visit the Waynesboro Heritage Museum to see important Waynesboro artifacts, photographs, maps, furniture, textiles, and more. Permanent and rotating exhibits feature various eras of city history and subjects like the railroad, Brigadier General Anthony Wayne, industry, and education. The museum is located in a restored 1908 bank, and even has an exhibit in a bank vault! 

Use the Traipse app to help you explore the Waynesboro Street Arts Trail. The puzzle hunt app will lead you to 20 impressive murals on an interactive two-hour tour. Waynesboro’s growing collection of urban art is created during the annual Street Arts Festival.

Another great way to discover important points in Waynesboro’s historic downtown is to download a brochure and take the self-guided Tree Streets Walking Tour. The Tree Streets are on the National Register of Historic Places. Visitors can see 400 homes, many built as early as the 1890s encompassing styles from Queen Anne to Classical Revival to Arts and Crafts and more.

Drinks, Dinner, and a Show


Start the night out right with a glass of Virginia wine and a cheese plate at The City Foxes Wine Bar + Market. Next, head to the Green Leaf Grill for a decadent meal with a Southern or Cajun flair and a big menu of classic cocktails. If you’re looking for something a little more casual, The River Burger Bar is a great spot to sit at the bar and chat with the locals and eat a gourmet burger or salad.

After dinner, head over to the historic Wayne Theatre, which has been showcasing the arts since 1926. Known best for its musical theatre productions, the Wayne also hosts live music and dance, a classic cinema series, science and history lectures, theater workshops, and art shows. Check the calendar for a complete list of events!


Sunday: Eat a Big Breakfast and Take a Long Walk Before You Head Home



Enjoy Waynesboro’s favorite breakfast or lunch at Weasie’s Kitchen, a classic diner offering generous servings of country-cooked deliciousness like omelets, pancakes, and combination platters. Another option for a yummy breakfast is Stella, Bella, & Lucy’s. You’ll love the fresh, made-to-order food and the unique artistic atmosphere. 

Work off your breakfast with a leisurely stroll along the South River Greenway. This paved shared-use trail hugs the South River and is enjoyed by walkers, joggers, and bikers. Make sure you look for birds and wildlife. If you like to fish, drop a line in the river, which is one of Virginia’s urban trout fisheries. Anglers and non-anglers alike should document the trip with a few photos at the fishing-themed LOVEworks sign, voted Best in Virginia!


We hope you enjoy your weekend full of small town charm, delicious food and drinks, history, art, and shopping without getting behind the wheel!


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