Outdoor Adventure Itinerary

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 heading to 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.

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 schedule before 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 Bar for 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 offers sites 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 River to 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 and class II rapids along the way and glimpse some of the historic homes and bygone industries of the city. 

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 our Maps page.