6 Scenic Road Trip Stops Along Skyline Drive

Take a trip along Virginia’s Skyline Drive, and you’ll see why President Herbert Hoover pushed so hard to have this scenic route constructed. This magnificent motor road through the Blue Ridge Mountains opened in sections throughout the early 1930s, built largely by Civilian Conservation Corps workers who not only graded slopes, constructed stone walls and overlooks, but also planted thousands of trees along the roadway.

Completed in 1939, just four years after the establishment of Shenandoah National Park, which it passes through, this epic 105-mile-long road trip travels along the crest of the Blue Ridge Mountains from Front Royal in the north down to Rockfish Gap near Waynesboro. Here, at its southern terminus, it connects to the even longer Blue Ridge Parkway, opening a whole other world of adventure.

To help convince you that this bucket list road trip is worth considering (it really is!), check out our list of scenic road trip stops along Virginia’s Skyline Drive.

Front Royal: Gateway To The Blue Ridge

Not only is Front Royal the northern terminus of Skyline Drive, it’s also one of the prettiest small towns in the Shenandoah Valley. It’s well worth exploring this first stop on your drive, stocking up on snacks, gas, and even popping in for a chat with the friendly folks at the Front Royal Visitors Center. In addition to ideas about things to see in Front Royal, they’ll also provide maps of the area, including must-sees and hiking routes along Skyline Drive.

Explore the neighboring Front Royal Town Square, grabbing a selfie next to the Virginia Tourism LOVE sign, then go for a pint at the fun Virginia Beer Museum. Several old homes have also been preserved here, including the Belle Boyd Cottage, built in the 1850s and once home to a female Confederate spy.

Front Royal’s position on the Shenandoah River is another plus, as it’s a great spot for fans of kayaking and canoeing. It’s also a popular stop for hikers along the Appalachian Trail. Once you’re ready to hit the road, head south along Royal Avenue to Milepost 0 and turn onto Skyline Drive, past the Shenandoah Valley National Park North Entrance sign. The ticket booths will be next.

Shenandoah National Park’s North District

You’re now in Shenandoah National Park’s North District. While less of a single stop but rather a series of stops, this early 32-mile stretch of Skyline Drive is likely where you’ll pullover frequently for those wonderful views. The Shenandoah Valley Overlook, the first of 75 lookouts along the route, provides views over Front Royal and across the Shenandoah Valley as far away as West Virginia. It is, of course, an especially pleasing view in the fall season when the mountain slopes come alive with color.

Just a short drive away is the Dickey Ridge Visitor Center at milepost 4.6. Set in a building that once served as a dining hall in the park's early years, here you can check out exhibits about the park’s construction, load up on maps, and even participate in fun ranger-led programs.

Several lookouts and an hour or two further (depending on how often you stop), and you’ll come to milepost 31.5. Here, Skyline Drive intersects with U.S. Route 211 at Thornton Gap, marking the boundary between the park's North and Central Districts. If you’ve got the time, take a slight detour to the nearby Luray Caverns, the largest collection of caves in Virginia.

Skyland Resort

Stop at milepost 41.7 for a stay or walk around Skyland Resort. You’re now at the road’s highest point at an elevation of 3,680 feet. Established as a summer resort called Stony Man Camp in 1894, Skyland today features lodge rooms, cozy cabins (many with views over the valley), and a full-service dining room.

Several historic structures are worth peeking at here, too, including Massanutten Lodge. Built in 1911, pop in to check out its massive stone fireplace and the spectacular lobby views across the Shenandoah Valley 3,600 feet below.

Skyland is also popular with hikers who can access several trails, including the popular half-mile walk to Stony Man Summit. For a fun equestrian experience, Skyland Stables opens seasonally and offers several trail riding options. And for entertainment, there's even an amphitheater for performances and lectures.

Hawksbill Summit

At 4,051 feet, Hawksbill Mountain is the highest point in Shenandoah National Park. Thanks to Skyline Drive, getting to the summit is a moderate hike via the Upper Hawksbill parking area at milepost 46.7. The gentlest summit approach, it’s a two-mile out-and-back trail with about 520 feet of elevation gain that passes through shady forest before emerging at Byrds Nest Shelter No. 2, a stone shelter that’s perfect for catching your breath.

From the shelter, you’re almost at the stone observation platform at the summit, so have your binoculars ready. Spectacular 360-degree panoramic views take in Massanutten Mountain to the west, Stony Man to the north, and the rocky profile of Old Rag Mountain to the east.

Hawksbill is also one of the few places in Shenandoah where balsam fir grows, a tree that’s more common farther north in places like Canada. Plan to arrive early in the morning or near sunset to avoid the midday crowds.

Big Meadows

When you see milepost 51, you’ve arrived at the geographic and historic heart of Shenandoah National Park. Known as Big Meadows, this 150-acre expanse of open grassland certainly stands out from the surrounding forest. Archaeological evidence indicates that Native American hunters used controlled burns to maintain the meadow as far back as 8000 BC, attracting deer to browse at the forest edge.

European settlers continued the practice when they arrived in the 18th century, using Big Meadows as summer pasture for cattle. Today, the meadow supports wetlands that contain rare plants found nowhere else on the planet.

It was also here that President Roosevelt dedicated Shenandoah National Park on July 3, 1936. Pop into the Harry F. Byrd Sr. Visitor Center, named for the senator who championed the park's creation, for a look at displays about the ark’s creation, as well as exhibits about both its human and natural history. Big Meadows Lodge, built in 1939 using local stone and native chestnut for interior paneling, provides overnight accommodations with rooms featuring real stone fireplaces.

Waynesboro And The End Of The Line

At Rockfish Gap (milepost 105.4), Skyline Drive ends and Blue Ridge Parkway begins its 469-mile journey south toward Great Smoky Mountains National Park. It’s here you’ll find yourself with an opportunity to pop into the town of Waynesboro. Located at the base of the Blue Ridge Mountains and in the very same Shenandoah Valley you’ve been looking down at for the past few hours, it’s definitely worth taking time getting to know.

South River runs through the downtown and is so pretty that it has been designated a Virginia Scenic River. Take a stroll along the Greenway Trail through Constitution Park, and you’ll see for yourself just how pleasant it is. The nearby Blue Ridge Tunnel, an 1850s railroad tunnel restored as a linear trail park, ranks as one of the coolest hiking routes in the state and follows the old Virginia Central Railroad line through a nearly mile-long tunnel.

Downtown shops, breweries along the Shenandoah Beerwerks Trail, and public art scattered through a Street Arts Trail all add up to make Waynesboro a delightful final stop on your Skyline Drive adventure.

What Are You Waiting For?

One of the best bucket-list experiences in Virginia, Skyline Drive is an excellent getaway. Whether you’re looking to complete the route in a day or can stretch it out with some camping or a stay in a rustic resort cabin, you’ll want to take your time. And while these six selected stops will give you plenty of ideas and inspiration, they only scratch the surface. So do your homework… and go out and see what you can find.