WanderLove: A Road Trip Through Southwest Virginia

Wanderlust is defined as a strong desire to travel, but here in Virginia, we call that feeling WanderLove. And while travel doesn’t look quite the same this year, you can still explore Virginia’s endless beauty with an epic road trip!

Head to Southwest Virginia’s Heart of Appalachia region, where we’ve put together a six-day itinerary filled with outdoor fun, delicious restaurants, and picturesque driving routes for an unforgettable vacation in Virginia’s beautiful mountains! 

Day 1 & 2: Mountain View OHV Trail System; Saint Paul & Coeburn

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Photo Credit: Sam Dean, IG account: @sdeanphotos

A backroads adventure in Wise County begins where the pavement ends. Just off US 58 ALT W from Abingdon sits the picturesque town of Saint Paul. Use the town as your basecamp to explore Spearhead Trail’s impressive Mountain View Trail System by ATV, side by side, or dirt bike. 

Leave the work week in the rearview and check into the Western Front Hotel. This boutique hotel delivers modern amenities and an authentic Southwest Virginia experience. Skip the paperwork at check-in by taking advantage of the hotel’s online ATV reservation and permitting system. Bringing your own ATV or other Off-Highway Vehicle? The hotel has plenty of parking. 

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Photo Credit: David Robinson

After getting settled in your room, head over to Sugar Hill Brewing Company for a comfort food dinner that goes above and beyond standard pub fare. Craft beer enthusiasts will also love their extensive selection, all of which are brewed on-site. 

On day two, head out early to hit the trails! Naturally, Saint Paul is an ATV-friendly town. Grab a trail map from reception, hop on your OHV, and ride through Saint Paul’s quaint downtown district to reach the Mountain View trailhead. Looking for an easy to moderate ride under a cool canopy of trees and foliage? Follow the green or blue marked trails. For experienced riders seeking a heart-pounding, seat-shaking trail ride through mud and rock, follow the black trails.

Whichever trails you choose, be sure to head in the direction of the connecting ATV-friendly town of Coeburn for a well-deserved lunch. Locals and visitors alike agree that Frosty Bossie has the best food in town. 

After lunch, explore Coeburn’s historic downtown on foot. Find the “Crooked Road Mural” that depicts what the town would have looked like over 100 years ago, sit for a spell on the town’s giant rocking chair, and snap a picture with Coeburn’s LOVEworks sign near the old train depot. 

After getting your fill of town, head back to the Coeburn trailhead and spend the rest of the afternoon exploring the remaining mountainside trails before returning to the hotel. 

After a hot shower, you’re ready for dinner at Fat Boys Barbeque. Those hungry for unforgettable barbecue and a friendly, casual environment should make room for Fat Boys’ large portions. 

Back at the Western Front, end your night with s’mores around the campfire. 

Day 3: Backroads of the Cumberlands’ Tomahawk Route; City of Norton & Town of Wise

On your third day in Wise County, follow the Backroads of the Cumberlands’ Tomahawk route for endless thrills and unparalleled mountain views. Before setting out on your excursion, we recommend spending time and money for a stop into the Spearhead Trails office in Coeburn for tailored route advice and to purchase a Backroads of the Cumberlands map. 

With your map in hand, grab breakfast on the road and head toward the Tomahawk route. From here, decide where you want the day to take you. Along your route, you’ll have the option to walk or bike the Guest River Gorge Trail, walk the Little Stony National Recreation Trail and witness its impressive system of waterfalls; experience breathtaking views from the highest point in the Cumberlands atop the High Knob Observation Tower; or trek into “Woodbooger Sanctuary” at Flag Rock Recreation Area. 

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Photo Credit: Brad Deel, IG account: @brad.deel 

Looking for adventure on two wheels? Flag Rock Area Trails allow mountain bikers to travel through 10 miles of rhododendron thickets, past giant sandstone boulders and cliffs, and through beautiful hardwood forests.

Or, if you are a serious hiker looking for a more intensive, full day or multiple day backpacking trip, don’t miss the Chief Benge Scout Trail. This 16.6 mile (one way) trail features rare high elevation plant and bird species, two lakes for swimming, and several beautiful mountain streams and waterfalls. Seven trailheads serve the Chief Benge Scout Trail, offering many access and exit points along the Tomahawk back road route. 

Whether you spend two hours or two days exploring the Tomahawk route is totally up to you! Campers hoping to lay out under the clear night sky are welcome at High Knob Recreation Area

When you get hungry, head down the mountain toward the City of Norton. Stop in here at one of several great restaurants, or continue onto the Town of Wise where you can chow down on pizza from either Moon Dog Brick Oven or Roma’s Restaurant & Pizzeria

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Ready to put your feet up? Check into The Inn at Wise.

With a quick nap, you’ll be ready to explore the community of Wise. If you’re craving local culture (and a glass of wine), make the quick drive to Mountain Rose Vineyard. The first ever winery in Wise County, Mountain Rose Vineyard’s history is as good as its wine! Planted on reclaimed mine land, the vineyard enjoys an abundance of minerals in its soil and crisp and dry autumn weather due to higher mountain elevations. This combination makes for very fruity, complex, and smooth wines. Try their signature “mines to wines” collection that features fun coal seam themed names, such as Jawbone and Pardee. 

Day 4: Backroads of the Cumberlands’ Thunderstruck Route; Town of Big Stone Gap

No need to check out of The Inn at Wise this morning – today’s ride will bring you back full circle! Just grab the essentials (keys, wallet, fishing pole…) and you’re ready for the day!

Of course, you should never adventure on an empty stomach. If a warm breakfast is calling your name, the hotel’s Corner Diner is located on the main level and offers classics like pancakes, biscuits and gravy, and a local delicacy, the bologna and egg biscuit!

When you’re ready to burn off those calories, buckle up and hit US 23 S. Today’s adventure will take you in and around the charming town of Big Stone Gap on the Thunderstruck route. A word to the wise – a four-wheel drive vehicle is needed for today’s ride! Turn left off the highway onto Powell Valley Road. Drive slowly – both to take in the stunning mountain views and to keep rubber on the road around the hairpin turns! 

Having made your descent safely down the mountain, you’ll now be tucked in the scenic valley between Powell Mountain and Little Stone Mountain. The landscape here transforms to gentle, sloping pastures dotted with wooden barns and farm animals. Simply dubbed “the Valley” by locals, this quiet farming community leads to the Big Cherry Reservoir and recreation area. 

Using the Backroads of the Cumberlands map you purchased the day before (see, money well spent!), follow the gravel road through the Thunderstruck route to reach the reservoir and its surrounding thrills. Consider the Big Cherry area your own personal playground. This 2,200 acre park features a 250 acre lake stocked with bass, trout, and muskie; multiple hiking and biking trails; scenic overlooks; and public hunting lands. Bring your gear and get out onto the water or into the wilderness. 

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Photo Credit: Joshua Moore, IG account: @jtm71

Choose to spend your entire morning exploring Big Cherry, or on a warm day, hop back in your vehicle and continue toward the community of Fort Blackmore. Here, at the end of a strenuous 1.8 mile trail, reach the blue-green water of the Devil’s Bathtub. This natural wonder draws visitors from around the country each year, and for good reason. The crystal-clear water feature is a popular spot for swimmers looking to take a refreshing, icy plunge and photographers hoping to capture its wild beauty. But take heed: this is not a trail for the faint-hearted or weak-kneed. Hikers will cross a stream about a dozen times, scramble over rocks, and trudge uphill to reach the tub. If you decide to take this hike on, go prepared. Wear appropriate shoes and clothing and pack a dry set of each to change into afterwards. Follow local guidelines about parking. For more information or to check on water levels, call the Clinch Ranger District of the Jefferson National Forest at 276-328-2931. 

In the evening, backtrack the Thunderstruck route to reach Big Stone Gap. Depending on time of day, grab lunch or dinner at Curklins. If you’re in the mood for music, check out the Big Stone Gap General Store & Café’s live music schedule! With a drink in hand, sit back and enjoy as regional musicians play both old favorites and originals. 

Take an after dinner stroll alongside the Powell River on the Greenbelt trail or, if you want to give your legs a rest, drop into the Southwest Virginia Museum Historical State Park or the Harry W. Meador Jr. Coal Museum for a taste of local history. 

If Big Stone Gap’s charm reminds you of the setting of a romance novel…you’d be right! Stop into the Big Stone Gap Visitor’s Center to learn more about local author Adriana Trigiani and her bestselling Big Stone Gap Series! The friendly volunteer staff are always happy to answer any of your questions about the town.

As you head back to your hotel for the night, stop at the Powell Valley Overlook to watch a spectacular sunset play out across the mountainside and the Valley below. As night sets in, look to the sky. The absence of big city lights makes this an ideal place to stargaze and watch for shooting stars! 

 Day 5: Backroads of the Cumberlands’ Lovelady Route; Pennington Gap & Ewing

No trip to Southwest Virginia is complete without a visit to Lee County. The westernmost tip of the Commonwealth of Virginia, Lee County played a crucial role in American colonial history as early settlers crossed through the Cumberland Gap on the Wilderness Road forged by Daniel Boone. Reserve your final two days in the region for exploring the rich history of the area. 

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Photo Credit: Scott K. Brown

To reach Lee County, depart from Wise and travel on US 23 S and US-58 ALT for approximately 26 miles. Turn onto State SR 621, the start of the Lovelady route. From here, enjoy the scenic drive along the edge of Jefferson National Forest land. Choose to stop and make camp by RV or tent at Cave Springs (seasonal) or Leeman Field RV Park. If a cabin or yurt are more your speed, hold out for Natural Tunnel State Park just across the Scott County border. 

All unpacked, stop into Lee County’s largest town of Pennington Gap for a quick lunch at Charly’s. Don’t linger too long in town (return for dinner and a show once night falls!), rather save your daylight for exploring Wilderness Road State Park or hiking to the famous Sand Cave! Both sites can be accessed from the community of Ewing, VA, so head that direction by way of US 58 W. 

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Photo Credit: Harold Jerrell

Wilderness Road State Park offers visitors a look at life on Virginia’s 1775 frontier with an outdoor living history museum. The park also links to the larger Cumberland Gap National Park via an 8.5-mile Wilderness Road Trail that is open to hikers, bikers, and horseback riders. 

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Photo Credit: Michael Speed, IG account: @photosbyspeed

If you’re up to the task, a 3.9-mile uphill hike originating from Thomas Walker Civic Park will lead you to the opening of a magnificent Sand Cave reminiscent of the Great American West. This giant rock formation, carved by the elements over time, puts on a show with its spectacular ceiling of green, gold, and red. Below your feet, 1.5 acres of powdery, cool sand makes for a perfect resting spot after a strenuous hike.

Head back to Pennington Gap for dinner and a cool drink at Rooster’s Pub. If you’re in town on a show night, walk across the street to the Lee Theatre to wind down your day. 

Day 6: Duffield & Pennington Gap

On your final day in Southwest Virginia, hop across the Lee County border to Duffield in neighboring Scott County via US-421 S. If you’re starting to feel the week’s adventures catching up to you, don’t be afraid to sleep-in this morning – Red Stone Drive-In serves breakfast all day!

Located next door to the restaurant is Natural Tunnel State Park. More than 850 feet long and 10 stories high, Natural Tunnel was naturally carved through a limestone ridge over thousands of years and was once called the “Eighth Wonder of the World” by William Jennings Bryan. Take the chairlift down to the tunnel floor to get the best view!

After snapping a few pictures, leave the main park area by car to find the park’s satellite location, the Daniel Boone Wilderness Trail Interpretive Center. Here, put your week’s visit into perspective by learning about the important role Wilderness Road and the Southwest Virginia region played in America’s westward expansion. Situated directly in front of Kane Gap, one of the last undeveloped portions of the Wilderness Road, the center offers a glimpse of the rough, unforgiving terrain early settlers traversed on their way to Kentucky.

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Photo Credit: Keith Lanpher

Finally, as your weeklong journey comes to a close, reflect on your adventures at Axe Handle Distilling in Pennington Gap. This family owned distillery operates out of an authentic log cabin structure and specializes in bourbon and rye whiskey distilling. Venture into the tasting room to sample their products and learn about the distilling process from the experts. Order a drink, settle into a rocking chair on the wrap around porch, and contemplate your next visit to Southwest Virginia! 

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