featured image best stops

6 Must-See Stops on a Shenandoah Valley, Virginia Road Trip

Estimated reading time: 4 minutes

Filled with quaint towns, stunning vistas, and historic sites, the Shenandoah Valley is one of America’s favorite getaways.

Offering tranquil landscapes, historic Civil War battlefields, and quaint colonial-era towns, the Shenandoah Valley is packed with can’t-miss sights. If you’re planning on driving through the Shenandoah Valley, check out this guide to discover the best stops, restaurants, and activities, so you can put together the perfect itinerary.

driving the shenandoah

Driving the Shenandoah

Understand: Things to Know to Plan the Road Trip

If you’re wondering when to drive the Shenandoah Valley, consider what activities catch your interest. For outdoors enthusiasts and festival-goers, summer is the best time to visit the Shenandoah Valley, as travelers can tube the rivers, explore the area by horseback, hike the Appalachian Trail, and pop by events such as the Winchester Greek Festival and the Shenandoah Valley Blackberry Festival.

Autumn is the best time for a drive along Skyline Drive, as the dazzling fall foliage and the blooming wildflowers provide an awe-inspiring backdrop, while spring brings comfortable temperatures and fresh breezes, making it the perfect time to hike the Stony Man Trailhead. Winter travelers wondering what to take on a road trip could pack boots, hiking poles, and cross-country skis to explore the icy wonderland of Big Meadows, or just a good book a bottle of wine if they plan on unwinding in the spas or cozy B&Bs.

hiking in the shenandoah

Hiking in the Shenandoah Valley

Skyline Drive/Shenandoah National Park

Stretching over 105 miles, offering 75 overlooks, and designated as a National Historic Landmark, Skyline Drive is considered one of the country’s most beautiful routes. A car journey along the route is particularly stunning in autumn, when leaf-peepers head down from D.C. to take in the extraordinary foliage. Skyline Drive runs from Front Royal to Rockfish Gap, and there are so many interesting pit stops and activities along the way that you’ll lose track of how many miles you’ve covered: hike the famous Appalachian Trail, visit President Herbert Hoover’s former retreat at Rapidan Camp, and work up a sweat on the Bearfence Rock Scramble.

Skyline Drive cuts through Shenandoah National Park, a vast park spread across 75 miles of land in the Blue Ridge Mountains. Shenandoah National Park is one of the country’s best stops for hikers, but visitors of all stripes will find a range of invigorating activities. Nature lovers will discover plenty to appreciate on Old Rag Mountain, bird lovers can spot red-tailed hawks and barred owls, and stargazers will discover an out-of-this-world experience with regular presentations and star-watching nights: there’s even an annual Night Sky Festival. Of course no road trip in the Shenandoah Valley would be complete without seeing its famous waterfalls, so grab the camera and snap some memorable pics of Lewis Falls and Dark Hollow Falls, which look especially remarkable in the stillness of winter.

If you’re looking for accommodations in the heart of the action, one of the best stops is Big Meadows Lodge, a rustic property right off Skyline Drive.

Beerwerks Trail/Waynesboro

What’s the best place to visit in the Shenandoah Valley? Well, if you’re a fan of craft beer, the answer is ‘all of them’! Hitting the region’s Beerwerks Trail will allow you to explore the best stops in the Shenandoah Valley, one refreshing brew at a time. The Trail runs from Harrisonburg to Natural Bridge, and includes 15 breweries. So whether you want to pair an artisanal red ale with a spot of fly-fishing, or enjoy a Belgian Dubble before taking in a classical music concert, the Beerwerks Trail is a great way to choose your pit stops when driving in the Shenandoah Valley.

best stops in the shenandoah valley

Shenandoah in the Fall

Three of the Beerwerks Trail’s breweries are located in Waynesboro, a quaint town near the terminus of Skyline Drive. Waynesboro’s historic downtown is the perfect place to shop for a one-of-a-kind souvenir, pick up some original art at the P. Buckley Moss Gallery, or relax with a glass of regional wine, while the Plumb House Museum offers a chance to step back in time to the Civil War era. Waynesboro also hosts a range of great seasonal events, including the annual reenactment of the Battle of Waynesboro, and the Fall Foliage Festival, when the town’s streets come alive with craftsmen, food trucks, and entertainers. For the perfect stay, book a room at the Iris Inn Bead & Breakfast, an intimate, traditionally furnished property with individually decorated quarters, a fireside bar, and complimentary manager’s receptions.

Luray Caverns/Harpers Ferry

If you’re wondering what to see in the Shenendoah Valley, two of the top attractions are Luray Caverns and Harpers Ferry, a pair of bucket-list landmarks drawing visitors from around the Eastern Seaboard. Luray Caverns attracts half a million visitors a year, and the cool, subterranean landscape – one of the largest cave systems in the Eastern U.S. – is not only an amazing place for a one-of-a-kind wander, it provides a great opportunity to beat the summer heat. The town of Luray is also home to Gathering Grounds, a charming café/patisserie offering some of the best food in the Shenandoah Valley. Stop by to enjoy an espresso on the dog-friendly patio, and then spend the night at Mimslyn Inn Historic Hotels of America, a cozy, traditional property with a pool and a spa.

best stops in the shenandoah valley

The Shenandoah in the Spring

Harpers Ferry, meanwhile, was the setting for one of the Civil War’s defining moments – John Brown’s raid on a United States arsenal – and although the town itself has less than 300 residents, it’s packed with historic attractions, making it one of the best stops in the Shenandoah Valley. John Brown’s Fort is perhaps the most popular draw, but the John Brown Museum, the Civil War Museum, Harper Cemetary, and Arsenal Square are all notable attractions. The area’s not only rich in history, but also offers a wealth of activities for active travelers, including canoeing, kayaking, zip lining, and rock climbing.

Offering historic sites, charming small towns, and a spectacularly beautiful landscape, Shenandoah Valley, Virginia, is one of America’s great destinations. Book your accommodation through Expedia, and hit the road to the Shenandoah Valley today!

Expedia compensates authors for their writings appearing on this site, such compensation may include travel and other costs.


We live and breathe travel, and want to help you discover your next vacation by sharing trip ideas, creative destination inspiration, useful information about booking travel, and savvy advice about world-wandering. So dig in to our travel articles, and find your next destination.



Leave a Reply

Your email address will not be published. Required fields are marked *