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.

Locations Featured in Video: Thunderbird Cafe, Massanutten Resort, White Oak Lavendar Farm, Pale Fire Brewing Company, Mossy Creek Fly Fishing, By The Side Of The Road, Magnolias Taco & Tequila Bar, Bodo's Bagels, IX Art Park, North American Sake, Veritas Vineyard & Winery

Follow your WanderLove from Harrisonburg to Charlottesville for a scenic adventure through the Blue Ridge Mountains. Unlike previous WanderLove routes like the trips from Norfolk to Virginia’s Eastern Shore, Fredericksburg to the Northern Neck, or Roanoke to Abingdon through Southwest Virginia, there are two route options for this road trip itinerary. We cover a wide range of safe social distanced 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! 


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


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. 

photo credit: Larry W. Brown

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.

Photo credit: Chad Williams, @echadwilliams

Take in a little arts and culture during your stay in Harrisonburg as you follow the Harrisonburg Downtown Art Walk. This public art project includes over 30 murals and outdoor art works, showcasing the talent of local artists and the organizations who support them. 

Need more inspiration for the Harrisonburg leg of your journey? Follow our Three-Day Guide to Harrisonburg to find more to do in this incredible mountain town.

Harrisonburg Restaurants, Breweries, Wineries, & More


Photo credit: Chad Williams, @echadwilliams

Magnolia’s Tacos and Tequila BarMexican restaurant with over ten different types of tacos and an impressive tequila menu. Limited outdoor outdoor seating available on the restaurant’s rooftop. 

Clementine CafeRestaurant, bar, and live music venue in downtown Harrisonburg serving Southern classics as well as more than a dozen vegetarian and gluten-free dishes. Outdoor seating available on the restaurant’s patio. 

Jack Brown’s Beer & Burger JointRustic saloon-style restaurant serving unique burgers paired with a great selection of craft brews. 

Billy Jack’s Wing & Draft ShackCasual sister restaurant to Jack Brown’s that has an extensive list of craft beers from all over the world.


Heritage BakeryCozy and warm French-inspired bakery and cafe in downtown Harrisonburg.

Magpie DinerFull-service breakfast and lunch restaurant with a diner-inspired seasonal menu. 

Merge Coffee CompanyCoffee company that roasts their own beans; two cafe locations within Harrisonburg.


Pale Fire Brewing Co.Craft brewery in the heart of downtown Harrisonburg with outdoor patio seating. 

Brothers Craft BrewingFamily-owned craft brewery with four flagship beers and frequent limited series brews and collaborations. 

Cuban BurgerCuban/American cuisine.

Little Grill CollectiveWorker-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 PizzaFarm-to-table pizza restaurant offering thin-crusted pizza cooked in a traditional wood-fired oven. 

Harrisonburg Hotels, Resorts, & Other Lodging

Joshua Wilton House Inn & RestaurantRestored Victorian mansion in downtown Harrisonburg converted into an elegant bed and breakfast.


Hotel MadisonFull-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 & BreakfastBed & breakfast in an historic home that was built in 1885, just steps from the shops and restaurants of downtown Harrisonburg. 

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, many with outdoor seating sections that allow for plenty of social distancing. 

photo credit: Brantley Ussery, @jbussery

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

There are plenty of parks within Charlottesville that allow you to get out and enjoy the Great Outdoors while also avoiding crowds; 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. 

Photo credit: Chad Williams, @echadwilliams

Get a taste of local art in Charlottesville at IX Art Park, an outdoor park filled with murals and sculptures that is free to the public.

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 Thomas Jefferson’s Monticello is a must during your trip. After touring 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, is free to public use from 7am-7pm daily, and contains over seven miles of dog-friendly trails.

Charlottesville Restaurants, Breweries, Wineries, & More

The VirginianA Charlottesville tradition since 1923, serves lunch, dinner, and late-night food like sandwiches, burgers, and their signature crab cakes. 

MarieBette BakeryEuropean-inspired restaurant serving breakfast, lunch, and an array of baked goods. 


South Street BreweryCozy craft brewery and restaurant with an extensive, creative draft beer list. 

Soul Food JointHome-cooked Southern Soul food. 

MasServe simple, well-made dishes cooked with local, organic, and artisanal ingredients; the focus is traditional Spanish fare. 


Bodo’s BagelsPopular bagel franchise in Charlottesville with multiple locations. 

Ace Biscuit & BarbecueBarbecue restaurant in the Rose Hill neighborhood of Charlottesville. 

Lampo PizzeriaAuthentic Neapolitan wood-fired pizza restaurant in the Belmont neighborhood. 

photo credit: Our Local Commons

Three Notch’d Brewing CompanyCraft brewery and restaurant near Charlottesville’s Downtown Mall in the IX Art Park.

Vitae SpiritsFamily-owned craft distillery producing small batch spirits such as barrel-aged rum, gin, and liqueurs. 

Wineworks ExtendedMichael Shaps Winery tasting room close to downtown Charlottesville.

Charlottesville Hotels, Resorts, & Other Lodging

Graduate Hotel CharlottesvillePet-friendly boutique hotel on the Corner and across the street from UVA grounds. Contains a coffee shop and an on-site restaurant, Camp Ten Four.

photo credit: jack looney

Boar’s Head Resort573-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 InnPet-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 CharlottesvilleUpscale boutique hotel in downtown Charlottesville that allows pets. On-site restaurant, Renewal, is known for their locally-sourced farm-to-table cuisine.

Quirk Hotel CharlottesvilleBoutique art hotel in Charlottesville’s historic downtown. Several on-site drinking and dining options, including the Pink Grouse, a modern, seasonally-focused restaurant, and a rooftop bar. 


61 miles, approximately 1 hour 21 minutes

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, and an indoor/outdoor water park with twisting water slides. There are two 18-hole golf courses within the resort grounds, and you’ll spot lots of local wildlife at practically every hole, such as deer and groundhog. In both the summer and the winter, the tubing park is open, providing an outdoor adventure option that is fun for all ages. 

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 the South River Falls Trail, an 8.5-mile circuit that leads to waterfalls. Another hiking option is Bearfence Mountain, a moderate one-mile hike with a rock scramble that ends with 360-degree views of the park.


bearfence mountain

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. 

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 of Central Virginia as your backdrop, including Chisholm Vineyards at Adventure Farm, Montifalco Vineyard, and Reason Beer. Enjoy a leisurely drive through the countryside before arriving in Charlottesville. 

Restaurants, Breweries, Wineries, & More


Thunderbird CafeVintage diner with a classic 50’s theme serving an impressively large menu of “south meets west” cuisine. 

Purple Wolf VineyardWinery tasting room on a lavender farm outside of Harrisonburg. 

CrossKeys Vineyard & Winery150-acre vineyard open daily for tastings with on-site bistro serving appetizers, sandwiches, wraps, and entrees made from locally-sourced ingredients. 

Spirit Lab DistillingCharlottesville micro-distillery producing single malt whiskey and gin.

Reynard Florence VineyardFamily farm vineyard with picturesque views of the mountains offering wine tastings during select hours Friday-Sunday in a cozy tasting room. 


Barboursville VineyardAward-winning winery and on-site restaurant. Known for their Octagon wine, a red blend of Bordeaux grape varietals. 

Elkton Brewing CompanyCraft brewery opened inside an historic building that dates to the 1890s. Specialize in natural artisan beers. 


Cave Hill Farms BreweryFarm brewery that sits on over 350 acres just outside of Shenandoah National Park.  

Hotels, Resorts, & Other Lodging

Massanutten Resort6,000-acre resort about 20 minutes outside of Harrisonburg and just minutes from Shenandoah National Park with 12 on-site dining options, two golf courses, an indoor/outdoor waterpark, mountain biking and hiking trails, zip lines and an adventure course, and winter sports park with tubing available year round. Lodging options include rooms, condos, townhomes, and private cottages, accommodating groups of every size. 

Lafayette Inn & RestaurantHistoric landmark inn built in 1840 with seven unique rooms and a formal dining room. 

Lydia Mountain Lodge & Log CabinsPet 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. On-site restaurant Bearrr Appetit open Friday-Sunday. 


61 miles, approximately 1 hour 24 minutes

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.

photo credit: mark miller

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. The road is a difficult ride, so if you’re not an advanced cyclist, consider opting for a hiking adventure, instead. Big Run Loop Trail 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. 


Blackrock Summit

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 through Rockfish Gap Outfitters in Waynesboro and set out on the water. Try your hand at fly fishing on a guided tour with South River Fly Shop, another Waynesboro outfitters company, choosing routes along the South River, the Shenandoah River, the James River, the Jackson River, or within Shenandoah National Park. 

Restaurants, Breweries, Wineries, & More


Pollak VineyardsBoutique winery on a 98-acre farm west of Charlottesville making French-style wines. 

Septenary Winery at Seven Oaks FarmAdults-only historic farm winery open 11am-5:30pm Thursday through Sunday. 

King Family VineyardsFamily-friendly boutique winery in Crozet in the foothills of the Blue Ridge Mountains. Host polo matches on Sunday mornings between Memorial Day and mid-October.

photo credit: Shannon Terry

Starr Hill BreweryAward-winning craft brewery in Crozet west of Charlottesville; second oldest brewery in Virginia. 

The Market at BellairGas station and market off Route 250 known for their high-quality signature sandwiches. 


The Fishin’ Pig WaynesboroBarbecue restaurant serving sandwiches, platters, and an array of Southern sides.  

Hotels, Resorts, & Other Lodging

photo credit: Nikki Nargi

Stable Craft Brewing SuitesCraft brewery with four individual one- and two-bedroom guest houses with views of the Blue Ridge Mountains surrounding.

Afton Mountain Vineyards LodgingPet-friendly two-bedroom guest house and one-bedroom cottages located on a picturesque Virginia winery. 

The Iris Inn Bed & BreakfastPet-friendly Waynesboro bed and breakfast overlooking the Shenandoah Valley and located just three miles from Skyline Drive and the Blue Ridge Parkway.

photo credit:jumping Rocks Photography IG account: @jumpingrocksphoto

Need more ideas for road trips around Virginia? Check out our previous WanderLove getaways!