Step back in time and head to Waynesboro, Virginia to satisfy your inner history buff!
Start your trip with your prearranged tour of Fishburne Military School, the oldest military secondary school in Virginia. Following your tour, head to Wayne Avenue and explore the Waynesboro Heritage Museum. This museum details the history of the City from its beginnings, significant railroad history, memorable business and industries, banks, and schools. The media room offers continuous screenings, and don’t forget to browse the gift shop.
Are you getting hungry? Satisfy your cravings at The French Presswith one of their quality “bevvies” and some homemade paninis or thier famous biscuits and gravy. Next, explore the unique shops in our historic downtown district. Finish out the day with a performance at the Wayne Theatre, a recently restored Vaudeville-era theater that now hosts world-class performances. They also have an exhibit gallery with rotating exhibits by renowned artists.
Visit the Plumb House Museum (advance arrangements should be made at the Waynesboro Heritage Museum), the oldest frame structure in Waynesboro, which survived the Civil War battle fought just behind it, and the Waynesboro’s Black History Museum at Rosenwald (call ahead to schedule a tour). Complete theself-guided architectural tours, and treat yourself a sandwich and craft beer at Delly Up. You deserve it!
Waynesboro and the surrounding area boast a vibrant artistic and cultural scene, with everything from live theater performances, to galleries filled with beautiful works, to street art, and more.
This whole itinerary takes place in Waynesboro’s historic downtown. Go ahead and park in one of Waynesboro’s multiple free city parking lots and start exploring!
As you make all the stops on your itinerary, you can also enjoy theWaynesboro Street Arts Trail. With 10 works of art within walking distance downtown and nine more just a short drive away, this is the perfect activity to weave in your day. If you enjoy scavenger hunts and street art, you’ll love this!
Start by grabbing a sweet treat and a coffee atThe French Press. Then head to theWayne Theatre(also home to the first street art mural, Poochie) which has a long, rich history of drawing the arts to the Valley since opening in 1926 as a vaudeville house. In recent years, the Wayne has brought more than 300 high-quality performances and events to the community annually. Known best, perhaps, for its musical theatre productions, the Wayne also hosts other forms of performing art, a classic cinema series, science and history lectures, and curated art shows in its exhibit hall.
Right around the corner, the Shenandoah Valley Art Center has been providing exhibit and studio space to local artists since 1986. Each year, the SVAC hosts four to six community exhibits, nine members’ exhibits, and ten main exhibits, including the coveted 40UNDER40 show. Aside from the two galleries, visitors can view artists at work in their studios upstairs and shop for handcrafted trinkets in the gift shop.
If you need a break, The City Foxes Wine Bar + Market is the perfect place to take in some art while sipping a Virginia wine and noshing on charcuterie. The City Foxes is the perfect blend of classy and relaxing where you can pick up locally made art and goods!
Walk down the street to the P. Buckley Moss Gallerywhich celebrates the work of Waynesboro artist P. Buckley Moss, known for her “Valley style” watercolors. Moss’s work is largely inspired by the Shenandoah Valley’s people and scenery, especially the traditions of the Amish and Mennonites.
If all of this browsing has your creative juices flowing, schedule a private class for you and some friends at Make Waynesboro Clay Studio to learn the art of throwing clay and take home a special piece that you created!
Are you ready to eat yet??Head right down to East Main Street and dine at Patina Inspired Ialian. Located in the Virginia Metalcrafters Marketplace, play some old fashioned arcade games or check out a show at the Foundry or Basic City Beer Co. after dinner.
Brimming with historic charm and natural beauty, Waynesboro lies just three miles from the junction of the Blue Ridge Parkway, Skyline Drive, and Appalachian Trail. With mountains to the east and the Shenandoah Valley to the west, Waynesboro’s prime location offers adventurers an almost limitless combination of excursions to enjoy by foot, bike, or kayak. Breathtaking hikes and vistas await discovery on the Blue Ridge Parkway, and limestone caves offer explorers a thrilling glimpse of what lies underneath the mountains.
Day 1: Arrive
Stroll along the 1.2-mile South River Greenway located along the South River in downtown Waynesboro. Park at the city lot on the corner of Arch and Main, then descend to the river, where you’ll find the paved trail, loved by pedestrians, cyclists, and roller-bladers alike. The famous “fish deck” and LOVEworks sculpture make for great photo ops. You can also count on seeing some wildlife along the way.
Cap off your day with dinner downtown Heritage on Main for southern comfort food with a twist, and a menu that changes from season to season based on what’s fresh. Pair your meal with your choice of a craft beer or fun cocktail.
Day 2: Adventure
Start off your day by fueling up for the adventures ahead with a filling “country boy” breakfast at Weasie’s Kitchen, a local favorite.
After breakfast, you’ll be ready to take on the short but strenuous Humpback Rocks Trail. It’s located at mile post 5.9 of the storied Blue Ridge Parkway. There are a variety of trails you can hike from the same starting point, but the most popular is the nearly 2-mile out and back. With a steep incline of about 700 feet, you’ll be huffing when you reach the top, but the expansive views of the valleys below are worth the climb.
On your way back down the mountain, stop off at the Blue Ridge Tunnel Trail for a stroll through an old train tunnel. Don’t forget a flashlight and a jacket! The tunnel is dark and always at 50 degrees.
When your muscles are worn out, head back to Waynesboro for dinner and a brew at Basic City Beer Co., an industrial-meets-modern microbrewery housed in a reclaimed brass foundry, featuring a brick oven pizza from Billy Pie.
Day 3: Head Home
After a thrilling day of mountain climbing and mountain biking, you’ll be ready to rest by Day 3, so grab a scrumptious brunch and a “Better Than Bloody Mary” from The Fishin’ Pig on your way out of town.
Brimming with historic charm and natural beauty, Waynesboro lies just three miles from the junction of the Blue Ridge Parkway, Skyline Drive, and Appalachian Trail. With mountains to the east and the Shenandoah Valley to the west, Waynesboro’s prime location offers adventurers an almost limitless combination of excursions to enjoy by foot, bike, or kayak. The spring-fed South River flows through downtown, drawing anglers from all over the country looking to catch trophy-sized trout. In addition, breathtaking hikes and vistas await discovery on the Blue Ridge Parkway, and limestone caves offer explorers a thrilling glimpse of what lies underneath the mountains. No matter what kind of outdoor adventure you long for, Waynesboro is “divinely placed among the adventure” (Virginia Craft Brews Publication).
Day One
Kick off your adventure by trying your hand at one of Waynesboro’s specialties: fly fishing. The South River Fly Shop on Main Street offers full-service guiding and instructing for every skill level, as well as a wide selection of gear. In addition to full-day excursions along the Shenandoah, James, and Jackson rivers, they also offer guided trips into Shenandoah National Park. For today you’ll want to schedule a half-day excursion on the South River, which runs through downtown Waynesboro and is one of only two urban trout fisheries in the state. Once Tommy or Kevin lead you to the sweet spots along the river, we think you’ll agree that its stocked waters make it an angler’s playground!
For lunch, grab a massive “Virginia Slice” of delicious pizza from Benny Stivale’s downtown before stopping at Rockfish Gap Outfitters for a map of the Big Levels/Sherando mountain bike trail system. Located just 15 miles south of Waynesboro in George Washington National Forest, Sherando Lake has been dubbed the “jewel of the Blue Ridge.” Its campground, beach, and swimming area are the local go-to for family fun, while its network of trails entice thrill-seekers who want to get off the beaten path. Bikers will find more than 20 miles of singletrack trails and dirt/paved roads through majestic, deciduous forests. This is rugged terrain, so prepare appropriately—with either shock absorbers or aspirin! When your muscles are worn out, head back to Waynesboro for dinner and a brew at Basic City Beer Co.,an industrial-meets-modern microbrewery housed in a reclaimed brass foundry, featuring a brick oven pizza from Billy Pie.
Day Two
Get a leisurely start to your day with a diner-style breakfast at Weasie’s Kitchen. You may want to drink an extra cup of coffee, because you’re about to go where the temperature stays 54 degrees year-round. “Where History Runs Deep” is the apt motto for Grand Caverns, a national natural landmark in Grottoes, Virginia, 15 miles north of Waynesboro. Formed from underground water action in the region’s limestone rock, Grand Caverns claims to be America’s oldest show cave, in operation since 1806. Visitors can stroll through high ceilings and open caverns in their classic tour or sign up for an “Adventure Tour” through Fountain Cave. Fountain Cave was recently reopened to the public after almost 100 years, and visitors will be treated to a true caving experience that includes no interior lighting, a once-used rugged 1800s pathway, and a full outfitting of helmets, knee pads, and caving gloves. The two-hour Adventure Tours are only offered certain times of the year, so be sure to check their schedulebefore you go.
After yesterday’s mountain biking, your muscles could probably use a stretch. Stroll along the 2-mile South River Greenway located along the South River in downtown Waynesboro. Park at the city lot on the corner of Arch and Main, then descend to the river, where you’ll find the paved trail. The famous “fish deck” and LOVEworks sculpture make for great photo ops. You can also count on seeing some wildlife along the way. This trail, loved by pedestrians, cyclists, and roller-bladers alike, represents the considerable effort and dedication of citizens and city staff to connect the South River to downtown and city parks.
Cap off your day with dinner downtown at The River Burger Barfor an elevated burger experience, or a tasty salad or wrap. Pair your meal with your choice of a craft beer or fun cocktail.
Day Three
The Blue Ridge Mountains boast not only great hiking but also great rock climbing. Just south of Waynesboro, cliffs range from 30-300’ tall. According to Blue Ridge Mountain Guides, “the Blue Ridge Parkway has both rock and ice climbs with low angle slabs, which are perfect for beginners, and vertical to overhung walls suited for advanced climbers looking to push their abilities.” The Guide offerssites and climbs suitable for all ages and skill levels that will give you a taste of climbing and rappelling over the Shenandoah Valley. Check their handy website for more information on all of their exciting adventures.
A late afternoon paddle along the South River will close out your three-day adventure. The Waynesboro Water Trail is the newest addition to the city’s park system and allows visitors the chance to see the city from the vantage point of the water. Put in your canoe or kayak at Ridgeview Park and paddle the scenic four-mile stretch of the South Riverto the convenient take-out at Basic Park. Shorter trips can be taken by, if desired, by utilizing other river accesses along the water trail. This stretch of the river is perfect for beginners or those looking for an easy paddle. You’ll encounter class I andclassII rapids along the way and glimpse some of the historic homes and bygone industries of the city. If you need gear, talk to the folks at Rockfish Gap Outfitters.
Additional info
Find the perfect lodging for your getaway with our up-to-date list of hotels and inns with their availability here:Where to Stay.
Check the water table of the South River before planning your paddle. A PDF version of the Waynesboro Water Trail, along with maps of popular hiking trails and historical walking tours, is available on ourMaps page.
Sweeping ridge-top curves and sunset-lit country roads converge in one divinely placed mountain town. Waynesboro offers the perfect base camp for motorcycle touring, with multiple days of beautiful riding and evening entertainment.
Day 1: Skyline Drive
This 105-mile ride through the Shenandoah National Park dishes up a full day of banked curves, hills, and vista-filled straightaways. One of the most famous routes in the world, this can’t-miss ride includes plenty of mountain twists with pavement that is smooth and clean. Seventy-five breathtaking overlooks provide easy pull-offs for stretching and sightseeing, as well as access to over 500 miles of mountain trails.
Wildlife sightings are common, from black bear crossings to hawk migrations. Chilly temperatures at high elevation and early morning fog are regular mountain phenomena, so bring a warm jacket even in summer. Park amenities include hiking, camping, concessions, and gas at milepost 51 at Big Meadows Wayside. From your Waynesboro base camp enjoy a post-ride flight at Basic City Beer Co, where industrial funk meets handcrafted ales. Housed in a revamped metalworking forge, cracked window panes and open-air patios make room for evenings of live music and an assortment of wood-fired Billy Pie pizza, tasty sandwiches, and shareables like nachos and cheese plates.
Day 2: Country Roads
Begin any long day of riding with Weasie’s Kitchen’s famous all-you-can-eat pancake stack, and return in the evenings to exploreBenny Stivale’s, Heritage on Main Street, or Green Leaf Grillfor more favorite downtown dining.
Travel the country roads of the Shenandoah Valley to explore destinations such as Luray, Grand, and Shenandoah Caverns; Shenandoah and Eastside Speedways(right here in Waynesboro!); Port Republic and New Market Battlefields. Meander through the pastoral farmland, stunning mountaintop vistas, and charming downtowns of the Valley before arriving back in Waynesboro for dining, lodging, and relaxation.
Day 3: Blue Ridge Parkway
Waynesboro is the northern gateway to the Blue Ridge Parkway, a 469-mile ridgetop adventure connecting Virginia’s Blue Ridge Mountains with the Great Smoky Mountains in “America’s Favorite Drive.” With rugged mountains, long-range vistas, and the rolling plateaus of the Appalachian Highlands, this meandering parkway offers a gorgeous and relaxing drive no matter which sections you choose to ride.
Before hitting the road, hit Happ Coffee Roastersor Farmhaus Coffee Co. for a conveniently located great cup of joe and some breakfast followed by some antique browsing and thrift store cruising in downtown Waynesboro.
From Waynesboro, visit Humpback Rocks Visitors Center at milepost 5.8 for hiking and a historic living-museum. Milepost 60 provides a gift shop, restrooms, and restaurant as well as a flat stroll around Otter Lake. Nearby James River Visitor Center marks the lowest point on the Parkway and showcases the old canals along the James River. Gain 3,300 feet of elevation over 12 miles as you roll into Thunder Ridge Wilderness at milepost 75, plus enjoy a very short leg-stretching trail with views of the Allegheny Mountains. The Peaks of Otter lodge provides full-service dining at milepost 86, whether you are choosing to loop back to Waynesboro or continue a multi-day tour further south.
Escape the hustle and bustle of everyday life and enjoy some pampering in a city surrounded by natural beauty. Grab a few of your closest friends or family members and come to Waynesboro.
Start with brunch at Stella, Bella & Lucy’s – a cute and cozy spot downtown that always pleases the palate.
Scratch your shopping itch by checking out the wide variety of shops downtown, such as Initial Inspiration, where you can monogram just about anything and find tons of cute home goods and gift ideas. Feed your inner artist and be inspired by the works of art at the Shenandoah Valley Art Center on Wayne Avenue. Hop over to Pyramid to discover handcrafted charcuterie boards, locally made pottery, raw honey, handmade jewelry, a fine selection of herbal teas, and so much more. If you’re up for some treasure hunting, Alpha & Omega Antique Mall on Arch Avenue has an ever-changing inventory of primitives, furniture, collectibles, glassware, and more.
Make an appointment at Freda’s Skin Studio for a facial, lash extension, or a salt therapy session.
Get dressed up and spoil yourself with some good food and drinks at the Green Leaf Grill – featuring live music and boisterous entertainment.