WanderLove: A Shenandoah Valley Road Trip From Harrisonburg to Charlottesville

Wanderlust is defined as a strong desire to travel, but here in Virginia, we call that feeling WanderLove. To help you plan your next road trip vacation, we’ll be sharing a few of the most scenic and adventure-filled routes through the Commonwealth, including the best outdoor adventures, restaurants, and lodging options to add to your itinerary.

Follow your WanderLove from Harrisonburg to Charlottesville for a scenic adventure through the Blue Ridge Mountains. There are two route options for this road trip itinerary. We cover a wide range of activities in Harrisonburg and Charlottesville, then take you through the two fun-filled drives in between to fill your road trip vacation with even more memorable experiences! 

HARRISONBURG & CHARLOTTESVILLE

 There are two unique route options to travel between Harrisonburg and Charlottesville, but there is plenty to do inside these two cities, as well. 

Things to Do in Harrisonburg

Begin your journey in Harrisonburg, a college town home to James Madison University that is located in the Shenandoah Valley off of Interstate 81. Harrisonburg is well known for an abundance of outdoor activities; travel in virtually any direction from the downtown area and you’ll run into some truly spectacular hiking and biking trails. To the east of Harrisonburg lies Shenandoah National Park, while George Washington National Forest runs parallel to the west. 

Mountain biking is extremely popular in Harrisonburg, and within the city limits, the Rocktown Trails at Hillandale Park offer three different levels of difficulty that suit mountain bikers of every skill level. Designed according to the IMBA guidelines, these shared-use trails have six distinct loops covering over four miles of track. In addition to these trails, there are hundreds of miles of mountain biking trails, road rides, and gravel routes surrounding the city, making it a prime spot for mountain bikers and cyclists looking to spend a significant amount of time tackling the challenging terrain.

If you aren’t planning on packing your own, rent mountain bikes through Shenandoah Bicycle Company, located in downtown Harrisonburg.

Another option for outdoor sports within Harrisonburg is a round of disc golf at Westover Park. Bring your own discs to play the free 21-hole disc golf course, open to the public and set against the gorgeous backdrop of the mountains.

Take in a little arts and culture during your stay in Harrisonburg as you follow the Harrisonburg Downtown Public Art Tour. This public art project includes over dozens of murals and outdoor art works, showcasing the talent of local artists and the organizations who support them. 

Use our complete guide to visiting Harrisonburg for more Friendly City fun. 

Where to Eat in Harrisonburg

• Magnolia's Tacos & Tequila Bar—Mexican restaurant with over ten different types of tacos and an impressive tequila menu.
• Clementine Cafe—Restaurant, bar, and live music venue in downtown Harrisonburg serving Southern classics as well as more than a dozen vegetarian and gluten-free dishes. 
• Jack Brown's Beer and Burger Joint—Rustic saloon-style restaurant serving unique burgers paired with a great selection of craft brews. 
• Billy Jack's Wing and Draft Shack—Casual sister restaurant to Jack Brown’s that has an extensive list of craft beers from all over the world.
• Heritage Bakery & Café—Cozy and warm French-inspired bakery and cafe in downtown Harrisonburg.
• Magpie Diner—Full-service breakfast and lunch restaurant with a diner-inspired seasonal menu. 
• Merge Coffee Company—Coffee company that roasts their own beans; two cafe locations within Harrisonburg.
• Pale Fire Brewing Company—Craft brewery in the heart of downtown Harrisonburg with outdoor patio seating. 
• Feel the Rain Brothers Brew Co.—Family-owned craft brewery with four flagship beers and frequent limited series brews and collaborations. 
• Cuban Burger—Cuban/American cuisine.
• The Little Grill—Worker-owned restaurant known for their vegan and vegetarian food, as well as healthy home-cooked fare made with locally-sourced meats.
  
• Bella Luna Wood-Fired Pizza—Farm-to-table pizza restaurant offering thin-crusted pizza cooked in a traditional wood-fired oven. 

Where to Stay in Harrisonburg

• Joshua Wilton House—Restored Victorian mansion in downtown Harrisonburg converted into an elegant bed and breakfast
  
• Hotel Madison—Full-service pet-friendly hotel in downtown Harrisonburg with many rooms offering views of the surrounding mountains and city views. Amenities include an indoor pool, an on-site restaurant, and a cafe located inside the hotel.
• Friendly City Inn—Bed & breakfast in an historic home that was built in 1885, just steps from the shops and restaurants of downtown Harrisonburg. 

Things to Do in Charlottesville

The final stop on your Blue Ridge Mountain vacation, Charlottesville is another popular college town, home to the historic University of Virginia. If shopping is on your checklist, explore the Downtown Mall, an outdoor pedestrian mall that includes over 120 shops and 30 restaurants. 

To immerse yourself in the Charlottesville college vibe, wander around The Corner, a historic section of shops and restaurants right across from the University grounds. 

There are plenty of parks within Charlottesville that allow you to get out and enjoy the Great Outdoors. McIntire Park is pet friendly and includes a nine-hole public golf course and nature trails on the western end of the park, while Pen Park has eight tennis courts, an 18-hole golf course, and a 1.5-mile nature trail. 

Get a taste of local art in Charlottesville at IX Art Park, a park and outdoor art museum filled with murals and sculptures that is free to the public. Get a ticket to head inside and experience The Looking Glass, an immersive art experience that'll transport you to a magical wonderland. 

More outdoor adventures await in Charlottesville. The Rivanna Trail System is spread throughout the city, split into short trail rides that range from just over a half-mile to about two miles long. These routes can be combined to take you on a cycling adventure around Charlottesville.

And if you’re interested in history, a visit to Monticello is a must during your trip. After touring Thomas Jefferson’s iconic property, get out and wander the grounds, following the Saunders-Monticello Trail for an added outdoor excursion. The trail system occupies 89 acres of land and contains over seven miles of dog-friendly trails.

Keep filling out your Cville itinerary with our complete guide to visiting Charlottesville. 

Where to Eat in Charlottesville

• The Virginian—A Charlottesville tradition since 1923, serves lunch, dinner, and late-night food like sandwiches, burgers, and their signature crab cakes. 
• MarieBette Bakery—European-inspired restaurant serving breakfast, lunch, and an array of baked goods. 
  
• Mas Tapas—Serve simple, well-made dishes cooked with local, organic, and artisanal ingredients; the focus is traditional Spanish fare.
  
• Bodo’s Bagels—Popular bagel franchise in Charlottesville with multiple locations. 
• Lampo Pizzeria—Authentic Neapolitan wood-fired pizza restaurant in the Belmont neighborhood. 
• Three Notch'd | Brewery & Craft Kitchen—Craft brewery and restaurant near Charlottesville’s Downtown Mall in the IX Art Park.
• Vitae Spirits—Family-owned craft distillery producing small batch spirits such as barrel-aged rum, gin, and liqueurs. 

Find more top restaurants with our Charlottesville dining guide. 

Where to Stay in Charlottesville

•  Boar's Head Resort—573-acre resort on the outskirts of Charlottesville with an outdoor pool, on-site dining, an 18-hole golf course, and a wide array of guided outdoor activities. 
• Oakhurst Inn—Pet-friendly Craftsman-style hotel near the Corner with 35 distinct rooms, an outdoor pool, and a cafe/restaurant that serves breakfast, brunch, and lunch daily. 
• The Draftsman Hotel—Upscale boutique hotel in downtown Charlottesville that allows pets and has a top-notch restaurant, The Ridley.
• The Doyle—Boutique art hotel in Charlottesville’s historic downtown. Several on-site drinking and dining options, including a rooftop bar.  

OPTION #1: ROUTE 33/ROUTE 29 THROUGH MASSANUTTEN

61 miles, approximately 1 hour 21 minutes

Things to Do near Massanutten

Travel east on Route 33 out of Harrisonburg to Massanutten Resort, a four-season resort just west of Shenandoah National Park. During the summer months, the resort offers mountain biking trails of every difficulty level, hiking trails that lead to gorgeous summit views, zip lines and canopy tours with treetop bridges and hanging vines to swing through the woods, a massive arcade, golf courses, and an indoor/outdoor water park with twisting water slides.  

Continue east on Route 33 and, to explore Shenandoah National Park, take a detour to the Swift Run Gap Entrance of the park and set out on the iconic Skyline Drive. It costs $30 per vehicle to get into the park, but you can purchase an annual pass for just $55. If you drive north, stop and hike South River Falls, an 8.5-mile circuit that leads to waterfalls. Another hiking option is Bearfence Rock Scramble, a moderate one-mile hike that ends with 360-degree views of the park.

Head south for a quieter section of Skyline Drive, which is less developed but filled with scenic beauty. Check out three major waterfalls in a single hike when you conquer Browns Gap, a moderately difficult 4.5-mile hike. Trail markers are sparse and cell phone service is spotty within the park, so download or print out a map before arriving. 

Keep Hiking: Check out our must-do hikes in Shenandoah National Park. 

Once back on Route 33, follow your journey to Ruckersville, where you’ll pick up Route 29 towards Charlottesville. This section has multiple breweries and wineries that make for excellent spots for a picnic with the stunning scenery as your backdrop, including Chisholm Vineyards and Montifalco Vineyard. Enjoy a leisurely drive through the countryside before arriving in Charlottesville. 

More to Explore: There are several stunning wineries near Shenandoah National Park — here are our favorites. 

Where to Eat near Massanutten

• Thunderbird Cafe—Vintage diner with a classic 50s theme serving an impressively large menu of “south meets west” cuisine. 
• The Purple WOLF Vineyard—Winery tasting room on a lavender farm outside of Harrisonburg. 
• CrossKeys Vineyards—150-acre vineyard open daily for tastings with on-site bistro serving appetizers, sandwiches, wraps, and entrees made from locally-sourced ingredients. 
• Spirit Lab Distilling—Charlottesville micro-distillery producing single malt whiskey and gin.
• Reynard Florence Vineyard—Family farm vineyard with picturesque views of the mountains offering wine tastings during select hours Friday-Sunday in a cozy tasting room.
  
• Barboursville Vineyards—Award-winning winery and on-site restaurant. Known for their Octagon wine, a red blend of Bordeaux grape varietals. 
• Elkton Brewing Co.—Craft brewery opened inside an historic building that dates to the 1890s. Specialize in natural artisan beers.
  
• Cave Hill Farms Brewery—Farm brewery that sits on over 350 acres just outside of Shenandoah National Park.  

Where to Stay near Massanutten

• Massanutten Resort—6,000-acre resort about 20 minutes outside of Harrisonburg and just minutes from Shenandoah National Park. Lodging options include rooms, condos, townhomes, and private cottages, accommodating groups of every size. 
• Lafayette Inn & Restaurant—Historic landmark inn built in 1840 with seven unique rooms and a formal dining room. 
• Lydia Mountain Lodge & Log Cabins—Pet-friendly rustic lodge and cabin rentals with stunning mountain views. Fully furnished cabins have stone fireplaces and hot tubs and range in size from one-bedroom to five-bedroom cabins. 
  

OPTION #2: ROUTE 340/ROUTE 250 THROUGH WAYNESBORO

61 miles, approximately 1 hour 24 minutes

Things to Do in Waynesboro

The alternate route from Harrisonburg to Charlottesville takes you south on Route 340, a road running parallel to Shenandoah National Park and connecting to Route 250 near Waynesboro. While the previous Route 33 drive took you past the Swift Run Gap Entrance of Shenandoah National Park, this journey takes you past the southernmost entrance to Skyline Drive, Rockfish Gap.

As we mentioned previously, the southern end of Shenandoah National Park is all about the scenery, but there are a few outdoor opportunities within this section, as well. Skyline Drive is well known for its world-class cycling, with 105 total miles and over 15,000 feet in elevation gain.

Skyline Drive is a difficult bike ride, so if you’re not an advanced cyclist, consider opting for a hiking adventure, instead. Big Run Loop and Blackrock Summit are two popular hikes between the Swift Run Gap Entrance and the Rockfish Gap Entrance of the park. In addition to these scenic hikes, the Appalachian Trail runs past the Rockfish Gap Entrance, allowing you to complete a section hike of the trail during your road trip. 

Running parallel to Route 340 all the way through Waynesboro, the South River also provides several outdoor activities on your road trip from Harrisonburg to Charlottesville. Rent kayaks or stand up paddle boards ]and set out on the water. Try your hand at fly fishing on a guided tour with South River Fly Shop. 

Where to Eat near Waynesboro

• Pollak Vineyards—Boutique winery on a 98-acre farm west of Charlottesville making French-style wines. 
• Septenary Winery—Adults-only historic farm winery at Seven Oaks Farm in Greenville 
• King Family Vineyards—Family-friendly boutique winery in Crozet in the foothills of the Blue Ridge Mountains with polo matches on Sundays from Memorial Day through mid-October.
• Starr Hill Brewery—Award-winning craft brewery in Crozet west of Charlottesville; second oldest brewery in Virginia. 
• The Market at Bellair—Gas station and market off Route 250 known for their high-quality signature sandwiches.
  
• The Fishin' Pig—Barbecue restaurant serving sandwiches, platters, and an array of Southern sides.  

Where to Stay in Waynesboro

• Stable Craft Brewing Suites—Craft brewery with individual suites and cabins overlooking the Blue Ridge Mountains — plus great beer and food on-site. 
• Cottages at Afton Mountain Vineyards—Two-bedroom guest house and one-bedroom cottages located on a picturesque Virginia winery. 
• Iris Inn—Waynesboro bed and breakfast overlooking the Shenandoah Valley and located just three miles from Skyline Drive and the Blue Ridge Parkway.

Find more Virginia road trip ideas to get started planning your VA-cation.