Seven Must-Visit Small Towns in the Shenandoah Valley

The Shenandoah Valley region is a stunning landscape of rolling hills, lush farmland, and verdant vineyards, all against the majestic backdrop of the Blue Ridge Mountains. Whether you're an outdoor lover, a wine enthusiast, a history buff, or simply seeking a peaceful escape, these seven small towns in the Shenandoah Valley have something special in store for you.

Winchester

Winchester is known for its rich history and beautiful natural surroundings. Kick off your visit at the Museum of the Shenandoah Valley, where you can explore regional history and art exhibits. Be sure to check out The Trails at the MSV, a 2.3-mile art walk dotted with outdoor art installations. Stroll Old Town Winchester where you’ll find charming brick-lined streets, quaint boutiques, and inviting restaurants. Historical sites, like the Patsy Cline Historic House and George Washington’s Office Museum, allow visitors to explore the lives of iconic figures. For evening fun, Bright Box is the place to be for live bands, karaoke, dance parties, and comedy shows. 

Where to Stay/Eat:

The George Washington Hotel is a historic boutique hotel with luxurious amenities, like an indoor pool modeled after a Roman bathhouse. For dinner, you can’t go wrong with a local favorite like Violino Ristorante Italiano for delicious, authentic Italian cuisine. Check out the Service Station Grub Trail, a flavorful 12-stop food trail that features current and former gas stations serving up award-winning BBQ, acai bowls, and tip-top pizza slices. 

Front Royal

Front Royal is a fantastic destination for Civil War enthusiasts and outdoor lovers. As the northern gateway to Shenandoah National Park, take a scenic drive on Skyline Drive for breathtaking views across the Blue Ridge Mountains. Check out Skyline Caverns for an exciting underground experience, then grab a paddle – and a canoe – from Front Royal Outdoors and get on the Shenandoah River. History buffs will love exploring sites like Belle Boyd Cottage and Prospect Hill Cemetery. Pick up a driving tour guide at the visitor center for the Battle of Front Royal Driving Tour. If you enjoy craft brews, stop by the Virginia Beer Museum to learn all about the history of beer in Virginia, which boasts more than 200 craft breweries.

Where to Stay/Eat:

For an in-town stay, look to the Hampton Inn Front Royal at the heart of downtown.

Plan a cozy, romantic getaway when you book a room at Glen Gordon Manor, a luxurious retreat on the outskirts of town with a seasonal pool, an on-site spa, and a complimentary gourmet breakfast. For dining, indulge in upscale American cuisine at Element or head to Spelunker's, known for its delicious burgers and ice cream. Start your day off right with a full spread at L’Dees Pancake House.

Luray

Luray is a real gem, best known for the show-stopping Luray Caverns, an underground wonderland filled with incredible limestone formations like the Great Stalacpipe Organ, the world’s largest musical instrument. Once you’re back above ground, there’s so much more to explore, like the Car & Carriage Caravan Museum, Toy Town Junction, and the Shenandoah Heritage Village. When you’re ready for adventure, rent a canoe from Shenandoah River Adventures or enjoy a peaceful walk around Lake Arrowhead.

Luray is a stone’s throw from Shenandoah National Park, so cruise along Skyline Drive, where you can stop at scenic overlooks and tackle wooded trails, like the stretch of the Appalachian Trail that leads to Mary’s Rock for wide-open mountain views.

Where to Stay/Eat:

Enjoy a stay at the Mimslyn Inn, a historic hotel that combines classic elegance with modern amenities, like pillow-top beds and an on-site spa. When hunger strikes, head to Chop House Bistro for farm-to-table dishes crafted from seasonal, local ingredients. For something more casual, even family-friendly, settle in at Ollie Cat Café for chicken fingers and strip steaks.

Harrisonburg

Harrisonburg is a vibrant college town packed with history, arts, and outdoor recreation opportunities. Start your adventure at the Virginia Quilt Museum, where you can marvel at historic and intricately-designed quilts. Next, stroll through the Edith J. Carrier Arboretum, a colorful botanical garden with walking trails and seasonal blooms. On Main Street, pop in and out of charming shops, like The Lady Jane, which sells unique gifts, like charm necklaces and throw pillows. On Saturday mornings, don’t miss the Harrisonburg Farmers Market, a treasure trove of maple syrup, hot sauces, and raw honey, as well as fresh fruits and vegetables. At James Madison University, catch a game or enjoy a performance at the Forbes Center for the Performing Arts.

Where to Stay/Eat:

Experience upscale accommodations near James Madison University when you stay at the Hotel Madison. Treat yourself to a meal at the Local Chop & Grill House where you can savor delicious steaks and seafood that are sure to impress. At Clementine Café, an eclectic menu and inspiring craft cocktails await.

Waynesboro

Sitting at the gateway to Shenandoah National Park’s south entrance, Waynesboro is a perfect launchpad for outdoor adventures. It’s where Skyline Drive meets the Blue Ridge Parkway, rewarding visitors with scenic drives and easy access to hiking trails, including stretches of the iconic Appalachian Trail. For indoor explorations, look to the Waynesboro Heritage Museum and the Shenandoah Valley Art Center. Don’t miss the vibrant Waynesboro Street Arts Trail, which features stunning murals that add pops of color all across Waynesboro.

Nearby wineries, like King Family Vineyards and Cardinal Point Winery, offer wine tastings and live music.

Where to Stay/Eat:

For a romantic escape, the Iris Inn is a wonderful choice, offering breathtaking views of the Shenandoah Valley. For families, the Residence Inn Waynesboro is a great option, featuring an indoor pool and roomy two-bedroom suites. When hunger strikes, stop in The River Burger Bar, a laid-back spot known for gourmet burgers and craft beers.

Staunton

Staunton is known for its vibrant arts scene, rich history, and beautifully-preserved Victorian-style architecture, which gives the town a timeless feel. Home to the American Shakespeare Center and Blackfriars Playhouse, a re-creation of Shakespeare’s indoor theater, Staunton is a hub for theater lovers. History buffs will enjoy the Woodrow Wilson Presidential Library and Museum, as well as the immersive Frontier Culture Museum, an open-air living history museum. Creative souls can dive into the craft of glass blowing at Sunspots Studios or explore the Camera Heritage Museum, the largest camera museum open to the public. Cap off your day with a stroll on Beverley Street for boutiques and vintage shops, like Juniper Lane and Electric Retro.

Where to Stay/Eat:

Hotel 24 South is full of character and historic charm but also modern-day amenities, like comfy pillow-top mattresses, an indoor pool, and laid-back vibes at the 1924 Lounge. It’s also just steps from Zynodoa, a farm-to-table restaurant serving up creative Southern dishes, like bruléed cast iron cornbread and chicken liver parfait.

Lexington

Lexington is where history, nature, and equestrian culture meet. Wander through the charming downtown area to explore landmarks, like the Virginia Military Institute, Lee Chapel at Washington and Lee University, and the Stonewall Jackson House. Wade’s Mill, the state’s oldest commercial grist mill, offers a look into the region’s agricultural heritage, while Natural Bridge State Park reflects the beauty of the region with its awe-inspiring limestone gorge, hiking trails, and children’s discovery center. Lexington’s strong equestrian culture is celebrated at the Virginia Horse Center, which hosts horse shows and events year-round.

Where to Stay/Eat:

For a cozy boutique stay, check in to The Georges, a charming inn located in the heart of downtown Lexington, honoring two great Georges – Washington and Marshall. When it’s time to dine, Haywood’s offers Southern-inspired cuisine with a side of live music on weekends. For something more laid-back, head to Heliotrope Brewery, where you’ll find some of the best pizza in town and a welcoming, casual vibe.

There are many other small towns within the Shenandoah Valley worth exploring, and the best way to discover them is to fulfill your Wanderlove with an epic road trip! Share your adventure stories with us and tell us your favorite destination in Virginia's beautiful Shenandoah Valley.