WanderLove: A Northern Virginia Road Trip From D.C. to Culpeper

Wanderlust is defined as a strong desire to travel, but here in Virginia, we call that feeling WanderLove. To help you plan your next vacation through Virginia, 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. Explore Virginia’s endless beauty with an epic road trip!

The Washington, D.C. metropolitan area includes one of the most bustling parts of Virginia. If you live in this cultural hub, you may be looking for a slightly slower change of pace.

Our advice? Skip the highways and their potential traffic snarls and instead take Route 50 West towards Winchester, then head south to Culpeper on Route 522. This leisurely route may take a bit longer, but it will guarantee that the journey is just as much fun as the rest of the vacation. 

ROUTE 50: WASHINGTON, D.C. TO WINCHESTER

73 miles, approximately 2 hours

Start your journey with a few activities only a few miles from the capital in Alexandria and Arlington. Stop by the Torpedo Factory Art Center in Alexandria and browse works from local artists. In addition to the cultural immersion, you can also take in the views of the Potomac River from the center.

For a little active entertainment, conquer part of the Mount Vernon Trail by bike or by foot. This 18-mile paved trail winds along the Potomac River, spanning from Theodore Roosevelt Island to George Washington’s Mount Vernon, which you can tour to learn about the Founding Father and the hundreds of people who lived and labored on his estate. 

Head west on Route 50 towards Chantilly, where you can see over 200 air and spacecraft at the National Air and Space Museum Steven F. Udvar-Hazy Center. The museum offers free admission and has a $15 parking fee. 

If you’re traveling with kids, detour to Frying Pan Farm Park, which shows how a farm would have operated from the 1920s to the 1950s and pays tribute to Fairfax County’s rural roots. Kids can see (and sometimes even pet!) draft horses, chickens, pigs, goats, cows, sheep, rabbits, and peacocks. 

Antique lovers should spend some time in Middleburg, a charming small town in Loudoun County set against the backdrop of the Blue Ridge Mountains. There are over a half dozen antique shops located on Washington Street, the town’s main street, where you’ll find hidden treasures and gorgeous antique pieces to take home. 

Continue along Route 50 to Sky Meadows State Park in Delaplane. The 1,860-acre pet-friendly park combines history with outdoor adventure with 22 miles of hiking trails, access to the Appalachian Trail, and nine miles of biking trails. There are also 10.5 miles of bridle trails open for horseback riding, as well as fishing, picnicking, and primitive hike-in camping sites. The Sensory Explorers’ Trail, a short .03-mile trail for people of all ages and abilities, is a must. This trail encourages pedestrians to use all of their senses to traverse the surrounding landscape. 

Restaurants, Breweries, Wineries & More

Ambar Clarendon—Balkan small plates, recommended for group dining

Artie’s—Seafood and meat entrees

Chrysalis Vineyards—400+ acre pet-friendly winery in Middleburg with views of the Bull Run Mountains

Boxwood Winery—Located on Boxwood Estate, a National Historic Landmark and one of the earliest established farms in the historic village of Middleburg

Greenhill Vineyards—Adults-only boutique winery, charcuterie platters for purchase to pair with wine tastings 

The Red Fox Inn & Tavern—Virginia landmark established in 1728 offering hearty meals in an historic tavern setting

King Street Oyster Bar in Middleburg—Seafood restaurant & oyster bar open for lunch, weekend brunch, and dinner

Delaplane Cellars—Small boutique family winery

Wild Hare Cider Pub—Middleburg cider pub

Hunter’s Head Tavern—Historic tavern built circa 1750 with a traditional English pub menu featuring a wide selection of on-tap beers and local and imported wines

James Charles Winery & Vineyard—Beautiful winery with expansive vineyards, apple orchards, and rolling hills

Winchester Ciderworks—Cidery tasting room on a gorgeous orchard outside of Winchester producing English-style hard ciders

Benny Meleto’s—Pizzeria known for their oversized slices

Hotels, Resorts & Other Lodging

Salamander Middleburg—Upscale resort set on 340 acres in the foothills of the Blue Ridge Mountains. Pet-friendly accommodations available, indoor and outdoor pools, and an award-winning restaurant on site 

Vander—Go all in on your adventure when you rent a camper van from Vander, based in the Washington, D.C. area. The ultimate in comfort and convenience, these vans give you the freedom to sleep practically anywhere and wake up to Virginia's most beautiful outdoor spaces.

The Red Fox Inn & Tavern—Historic inn and tavern in Middleburg that was established in 1728

Goodstone Inn & Restaurant—Luxurious country inn with private rooms and cottages, as well as an on-site restaurant serving farm-to-table cuisine made from ingredients grown on the property and an outdoor pool

The Ashby Inn & Restaurant—Historic inn that dates back to 1829 in Paris, Virginia 

The George Washington Hotel—Originally built in 1924, a charming blend of history, modern amenities, and first-class service. Located just steps from the Old Town Walking Mall in downtown Winchester

Fuller House Inn—Historic mansion inn in Old Town Winchester built circa 1850

ROUTE 522: WINCHESTER TO CULPEPER

67 miles, approximately 1 hour 22 minutes

Spend some time exploring Winchester, a small Shenandoah Valley city located in the northern section of Virginia. Walk through Old Town Winchester, an outdoor pedestrian mall in historic downtown Winchester lined with shops and restaurants. 

Consider touring the Museum of the Shenandoah Valley to learn about the history and culture of the region. The museum includes galleries and exhibits, seven acres of formal gardens, and the Glen Burnie House, an historic home with sections originally built in 1794 and 1797.

Visit the Patsy Cline Historic House, the childhood home of the iconic American singer, to pay homage to the country music legend. 

Depart Winchester for Front Royal, where along the way you can get active on the Jim Barnett Park Disc Golf Course or the Rockland Park Disc Golf Course, both 18-hole disc golf courses that are open to the public. Bring your own discs if this is on your itinerary, and be ready for a little cardio, as these courses are very hilly. 

Take a detour (about ten miles) off Route 522 to visit Shenandoah River State Park. Situated on the South Fork of the Shenandoah River, the park has 5.2 miles of shoreline and over 1,600 acres of pristine mountain landscape. There are more than 15 miles of trails within the park open to hiking, biking, and even horseback riding, as well as primitive campsites and a full-service bathhouse. 

Another potential detour is the State Arboretum of Virginia. The site has a collection of over 6,000 types of trees and woody shrubs — including a third of the world’s pine species — and the largest collection of boxwood cultivars in North America. The grounds are open from dawn to dusk daily and are free to the public.

Traveling with kids? If so, Dinosaur Land is a must! This kitschy roadside attraction has been a road trip staple since 1969 and features more than 50 fiberglass creature statues. There is even a King Kong statue large enough that you can sit in the hand for a photo op! Before leaving, spend some time perusing the gift shop to bring home some one-of-a-kind souvenirs. 

Head into Shenandoah National Park at the Front Royal Entrance to Skyline Drive. This section has several popular hikes, like Dickey Ridge, a 5.3-mile hiking trail that starts right off the Front Royal Entrance at the Dickey Ridge Visitor Center. 

You’ve spent some time exploring Virginia’s mountains, but to truly marvel at the Commonwealth’s magnificent natural wonders, travel to Skyline Caverns outside of Front Royal. One of Virginia’s cavern systems open for tours, Skyline Caverns is famous for its Anthodite formations (gorgeous rock formations that resemble colorful flowers). 

Resuming your journey south on Route 522, you’ll hit another access point to Shenandoah National Park, the Thornton Gap Entrance, outside of Sperryville. From this entrance, you can reach some of the best trails in Shenandoah, such as Mary’s Rock, which runs over one of the most spectacular sections of the Appalachian Trail, Whiteoak Canyon, a trail that features six stunning waterfalls, and Old Rag, a popular circuit hike suited for more advanced hikers.

Leave the park and pick up Route 522 until you reach Culpeper. Spend some time walking around downtown, stopping into a few local shops and enjoying the laid-back vibe of this quaint small town. 

Looking for a once-in-a-lifetime experience while in Culpeper? Book a helicopter tour of the region through Skyline Heli Tours and soar above Culpeper and nearby Charlottesville, getting a bird’s eye view of the mountains and valleys below. 

Restaurants, Breweries, Wineries & More

Chester Gap Cellars—Picturesque winery offering tastings of their estate-grown Viogner, Merlot, Cabernet Franc, Petit Verdot, Petit Manseng, and several innovative blends

L’Dees Pancake House—Family-owned and operated restaurant known for their delicious breakfast fare, but also offering lunch and dinner menus

The Blue Door Kitchen & Inn—Inn and restaurant located inside an historic schoolhouse. Menu features creative dishes made from locally-grown, seasonal ingredients

Glen Gordon Manor—Winery and bed and breakfast overlooking Shenandoah National Park with an outdoor pool and an award-winning on-site restaurant

Gadino Cellars—Winery in the foothills of the Blue Ridge Mountains near the historic town of Washington

Old House Vineyards—75-acre farm and vineyard that hosts tastings in a beautifully renovated barn that dates to the 1800s

It’s About Thyme—Charming cafe serving European country cuisine in a casual old-world setting

Mountain Run Winery—Family and pet-friendly farm winery in Culpeper crafting wines and ciders

Belmont Farm Distillery—Moonshine distillery on a 189-acre farm outside of Culpeper

Three Blacksmiths—Upscale Sperryville restaurant crafting a fixed weekly dinner tasting menu out of locally-sourced, seasonal produce and goods

Copper Fox Distillery—Distillery in Sperryville that offers cocktail flights 

Rappahannock Pizza Kitchen—Sperryville wood-fired pizzeria

Hotels, Resorts & Other Lodging

The Inn at Little Washington—Luxury boutique inn that is also home to a Michelin-star restaurant

L’Auberge Provençale—French-inspired country bed and breakfast in the Shenandoah Valley with an upscale on-site restaurant

Inn at Vaucluse Spring—Accommodations include six guest houses amidst 100 acres in scenic orchard country of the northern Shenandoah Valley. Outdoor pool, pond with natural springs, and on-site restaurant that utilizes ingredients grown on-site

Thyme Inn—Downtown Culpeper inn with luxury suites located beside a restaurant and market

Locations Featured in Video: Delaplane Cellars, Dinosaur Land, Fuller House Inn, Sweet NOLA's, It's About Thyme, The Frenchman's Corner

Looking for even more inspiration for road trips around the Commonwealth? Check out our WanderLove road trips through Virginia from the mountains and valleys to the coast.