How to Explore Northern Virginia’s Wine Country in a Weekend

From Towns to Trails: Here’s why you should add an outdoorsy weekend in DC’s Wine Country to the top of your bucket list…

Located just over an hour west of Washington, DC, are some of the the most charming towns in Virginia… many of which you may have never heard of.

These charming towns call the foothills of the Blue Ridge Mountains home and make up the region (that you probably have heard of) known as Northern Virginia’s Horse & Wine Country. We spent Labor Day weekend exploring some of these towns and their hiking, biking, and tasting trails and had the best (boozy) escape from the city that we could’ve asked for.

If you’re looking for a fun day trip or weekend getaway destination from DC, keep reading, because this is the spot for you. We hiked, biked, ate, and sipped our way around Northern Virginia’s Wine Country, and when we say it it felt like a whole different planet even though we were just an hour outside of our nation’s capital, we mean it! And we rounded up everything you need to know to plan your trip.

Virginia is for Wine Lovers

With over 300 wineries state-wide (100 of which are in NoVA) contributing 1.37 billion dollars annually to the economy, Virginia’s wine industry is booming. The commonwealth’s wineries have been long known for their beautiful vistas, but they’re not just pretty places to drink a glass of wine anymore. With 70 different varieties of grapes grown throughout the state, the wines produced here are both diverse and delicious. Not to mention, Virginia ranks 6th in US wine production and has its own native grape, the Norton grape, which happens to be the oldest wine grape in the country. Watch out Napa Valley!

Now that you know Northern Virginia’s Wine Country is worth a visit, here’s how we recommend exploring the region…

We stayed in the most beautiful AirBnb in Upperville, Virginia (more on that later), which is located in Fauquier County just across the border of Loudoun County and about 15 minutes from the charming town of Middleburg, VA. In that area alone, there are over a dozen wineries, so we spent the majority of our time there.

That said, no matter where you stay in the region, there are two wine trails that will help you plan your visit:

Fauquier County Wine Trail

Fauquier County sits on the same latitude line as Napa Valley, California AND Southern Italy, so the grapes that are grown here are truly world class. The Fauquier County Wine Trail splits the area’s 20+ wineries up into four clusters. Our favorites along the trail are  Barrel Oak Winery & Farm Taphouse, Three Fox Vineyards, and Naked Mountain Vineyard.

Loudoun County Wine Trail

Loudoun County is home to 52 wineries and best explored via various different clusters as well. We’ve linked the full trail guide as well as a map if you’d like to plan your own route. We based our wine trail explorations around the Middleburg area and particularly enjoyed Boxwood Estate Winery and Greenhill Winery and Vineyards.

Honorable Mention: Northern Virginia’s Breweries

Northern Virginia may not be as well known for its craft beer scene as it is for it’s wine, but it’s certainly worth exploring nonetheless. With a growing number of breweries (and winery-brewery combos), each offering a unique experience and a diverse range of flavors, there’s something for every beer enthusiast to discover, so it’s only fair that we raise a glass to the thriving craft beer culture in Northern Virginia as well.

One particular Ale Trail that is worth checking out is Loudoun County’s LoCo Ale Trail. It is made up of 30 diverse breweries. Our favorites are Dirt Farm Brewing and Bear Chase Brewing. Both are located in Bluemont, VA and offer great beer, yummy food, and beautiful views.

We also really enjoyed spending some time at Lost Barrel Brewing. This brewery is located right outside of downtown Middleburg, both family and dog-friendly, and has a pretty extensive food and wine menu.

Three Fox Vineyards and Brewery also has great ambiance and offers beer and wine tastings and full pours. We stayed for golden hour on our first night in town, and it was absolutely beautiful watching the sun set over the rolling hills.

Must-Have Outdoorsy Adventures in Virginia’s Wine Country

Sky Meadows State Park

With opportunities for hiking, biking, camping, horseback riding, and stargazing, this 1,862-acre park offers a unique blend of historical charm and breathtaking natural beauty. The park’s gates are open daily from 8 a.m. to dusk, and the Visitor Center/Gift Shop is open Monday-Thursday 10 a.m.-4 p.m., Friday-Sunday 10 a.m.-5 p.m., and on evenings when the park holds astronomy programs.

For the Hikers:

This park boasts a 22 mile network of well-maintained hiking trails catering to all skill levels. For beginners and families, the Lost Mountain area provides an easy and enjoyable experience as does the Sensory Explorers’ Trail in the Valley Area. The Piedmont Overlook Trail offers breathtaking vistas of the Shenandoah Valley, while the North Ridge and South Ridge trails provide more of a challenging trek.

For the Bikers:

If biking through rolling wildflower-covered pastures sounds like your idea of a fun afternoon, Sky Meadows is the place for you. The park offers 9 miles of biking trails to choose from, but our favorite is definitely Rolling Meadows in the Lost Mountain area of the park.

For the Stargazers:

Sky Meadows is one of only two designated International Dark Sky Parks in Virginia, but because the park closes at dusk, there are only two options for enjoying a starlit sky here:

1) The park offers monthly astronomy programs. They’re family-friendly, three hours long, led by both members of the Northern Virginia Astronomy Club and NASA’s Jet Propulsion Lab (JPL) Ambassadors, and cover the importance of dark skies and light conservation and the latest news in astronomy. These experiences also allow time for guided stargazing. You can check out the schedule here.

2) The park also offers primitive/backcountry hike-in camping facilities which allow for a self-guided stargazing/astrophotography experience. Sites can be booked here.

For the History Buffs:

The land that is now Sky Meadows was once a part of a land grant from Lord Fairfax to the Ashby family in the 18th century, and to this day, the park includes several well-preserved historic structures which offer visitors a glimpse into the past.

Raven Rocks Vista

This is hands down our favorite trail in the area! It can be reached via the Appalachian Trail and crosses from Virginia into West Virginia.

To get to and from the summit, you’ll have to hike 5.7 miles and gain 1,500 feet of elevation. This hike is rated as challenging, but worth every step for the sweeping views that is offers, if you ask us!

Check out our most recent footage of this hike!

Bear’s Den Park Trail

If you’re looking for a trail that is a little less challenging, but still offers beautiful views of the valley, Bear’s Dan Park Trail is it! This 1.6-mile out-and-back hike is ranked as an easy route on AllTrails, and takes about 45 min to complete.

NOTE: As more and more people are reaping the benefits of Mama Nature, it is so important that we all educate ourselves on & practice Leave No Trace to keep all of our outdoor spaces beautiful. If you’re unfamiliar with these practices, we urge you to check out this post for more information.

Where to Stay in Virginia’s Wine Country: Raspberry Repose

If you’re looking to stay somewhere with a luxury feel and immaculate design, we couldn’t recommend Raspberry Repose more. We were invited to stay for the long weekend, and this property proved to be the most perfectly-located home-base. 

Located in Upperville, VA, just 15 minutes from downtown Middleburg, Raspberry Repose sits on on a 10-acre wooded property. It is surrounded by wineries and hiking trails, yet provides a private oasis for guests away from the hustle-and-bustle of nearby “downtowns.” The property boasts a soaking tub, covered indoor patio, outdoor fire pit, cornhole boards, and with four bedrooms and three-and-a-half baths, the ability to sleep 11, making it the perfect place to host family and friends.

Seth’s parents joined us on this trip, and after seeing the adorable bunk room equipped with games and toys for kiddos, we wished that our nephews would’ve been able to join us as well!

Bottom line, Northern Virginia’s Wine Country is an area that should not be overlooked for travelers based anywhere across the Mid-Atlantic United States (and beyond)! With its picturesque landscapes, beautiful mountains and valleys, award-winning wineries, and rich history, this destination offers the perfect weekend getaway for couples, friends, and families alike.

That said, we are already planning a trip back to take in the fall foliage from the vineyard’s vistas and the summit of Raven Rocks, so please let us know where we missed and where we must go next time in the comments!