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Take a WanderLove Road Trip Along the Skyline Drive to Waynesboro

Are you eager to leave the bustle of NOVA and spend a romantic weekend exploring scenic roads, trails and a cozy downtown with your sweetie? If you love to wander with your love, we have just the road trip for you. Plan a drive through Shenandoah National Park along the Skyline Drive and make your grand finale weekend in Waynesboro before you head home.

Route Section #1: Skyline Drive

The magnificent Skyline Drive stretches 105 miles from Front Royal to Waynesboro along the Blue Ridge Mountains through Shenandoah National Park. Download the park’s app for maps of trails, campgrounds, waystops, and locations of the more than 70 overlooks offering chances to stop and admire views of the Shenandoah Valley and the Virginia Piedmont.

Where to Eat

There’s no better place to enjoy a romantic picnic than on the top of the world, and you’ll find wayside food stops every 25 miles for snacks, groceries, and carry-out meals. If you’re looking for sit-down dining try Skyland’s Pollock Dining Room and the Mountain Taproom for traditional and seasonal regional favorites made with locally sourced ingredients. Big Meadows Lodge also provides diners with a chance to sample Southern specialties as well as lighter fare.

Where to Stay

The most stylish place to stay in SNP is Skyland Lodge. Located at the highest point along the Skyline Drive, you have your pick of rooms, suites, and cabins, including pet-friendly accommodations. If you’d rather sleep with a view of the stars, Big Meadows Lodge or Campground is your ticket.

Must-See Sights

Grab a map from the Thornton Gap Visitor Center, or download one on your phone. With over 70 overlooks to choose from, you’ll be hard-pressed to pick the best view! Keep a lookout for:

Mary’s Rock Tunnel (Milepost 32.4) In 1932, workers from the Civilian Conservation Corps took three months to blast 670 feet through the granite.

Milam Gap (Milepost 52.8) Hike an easy two miles to visit Rapidan Camp. Visitors can make reservations for ranger-guided tours of President Hover’s 1929 fishing camp.

Calf Mountain (Milepost 98.9). Just a few miles before leaving SNP, stop at the Calf Mountain overlook for one last spectacular view of the Shenandoah Valley from above.

Outdoor Options

Shenandoah National Park offers more than 500 miles of some of the best hiking in the country and many trails can be accessed from the Skyline Drive. Bikers are welcome to travel the Skyline Drive and other paved areas of the park. Check regulations for fishing if you’d like to bond over a hook.

Route section #2: Waynesboro

Waynesboro is called the Gateway to Skyline Drive and the Blue Ridge Parkway, and at just four miles away from the entrances, it’s an ideal place to rest and replenish after a long day of driving. Waynesboro has much to offer the roadtripper, including a charming and vibrant downtown filled with shopping, dining, and culture as well as a number of outdoor experiences, all within view of the beautiful Blue Ridge Mountains.

Where to Eat

The first thing you should do is grab a drink to refresh and plan the next stage of your adventure. For a unique experience, check out Blue Ridge Bucha, which serves up its kombucha, (naturally carbonated, fermented tea) in a number of flavors. Nearby Basic City Beer Co. offers taproom or outside seating for sipping craft beer and earning a stamp for your Shenandoah Beerwerks Passport. If wine is more your style, make your way to Barren Ridge Vineyards, where you can sip wine on the terrace and admire one of the prettiest sunset settings in the area.

Whet your appetite at Heritage on Main with one of their 31 specialty cocktails and a treat like crab cakes, steamed shrimp or fries poutine. Choose a home cooked main course like Pennsylvania lamb with apple cider gastrique, cajun shrimp polenta, or even a burger or sandwich.

If burgers are your jam, you’re in for a treat at Waynesboro’s newest eatery The River Burger Bar. This classy joint serves both classic and gussied up Angus beef burgers (think fried green tomato and goat cheese with red onion, spicy aioli and arugula) and high-end pub fare appetizers as well as wine, beer, and cocktails.

Where to Stay

Make reservations to cuddle up at the Iris Inn, where guests are treated to incredible views overlooking the Shenandoah Valley as well as personal services and high-end amenities. The 19-acre property boasts newly renovated suites with king-sized beds and deck access in the main inn. Guests can also choose from private cottages or couples-only cabins perched at the edge of the mountain with walls of windows, screened porches, and hot tubs. Upon check in, guests are welcomed with wine and cheese. The inn serves a three-course gourmet breakfast every morning. You can even amp up the romance factor by adding a special anniversary package containing wine and treats.

Must-See Sights

Downtown Waynesboro is home to many independently owned shops and businesses. Take home something special to decorate your love nest from Initial Inspiration or Alpha & Omega Antique Mall. Find your new favorite local artist in the gallery (and gift shop) at the Shenandoah Valley Art Center.

If you bond over a mutual love of history, visit the Waynesboro Heritage Museum, which tells the story of Waynesboro through several galleries containing exhibits on the railroads, business and industry, schools and education, and more.

Outdoor Options

Take a leisurely stroll (or bike ride) down the South River Greenway, which stretches 1.2 miles along the South River. You’ll enjoy views of the city, the Blue Ridge Mountains, and the water, which is habitat to fish, birds, and human paddlers. Stop and pose for photos by the river-themed LOVEworks sign. Another way to enjoy this section of Waynesboro is to rent a kayak from Rockfish Gap Outfitters and float down the 4-mile section of the South River that makes up the Waynesboro Water Trail.

You’ll need to head into the country a bit to visit Star B Stables, but if you want to add an off-road component to your road trip, there’s nothing better than a gentle horse and a peaceful trail ride through the Valley.

If you’d like to stretch your legs on a serious (but short) hike, head up Afton Mountain to the Humpback Rocks Visitor Center. Tour the interpretive farm that represents an 1890s mountain settlement and then climb the steep mile up to the rocks where you’ll have a heartstopping view of the Shenandoah and Rockfish Valleys.

What Next?

Waynesboro is beautiful in all seasons. Make sure you plan your next road trip for when the leaves are full of fall colors. Check out other Virginia road trips at

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