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Loudoun County Magazine
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  • Arts & Entertainment
    • Arts & Entertainment
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  • Attractions
    • Best Places
    • Civil War History
    • Equestrian Venues
    • Family Attractions
    • Festivals
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    • Places to Stay
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    • Restaurant Guide
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    • Wine Tours
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Loudoun Wine inspired Travel -- Day One

Self-driving tour

 When you embark on a self-drive tour across D.C.'s Wine Country, you'll have over 50 wineries and vineyards to choose from while discovering the beautiful Loudoun region by car. This tour begins along Route 15 in Leesburg at Stone Tower Winery. You'll continue by car to Cana Vineyards and Winery, with a stop at Greenhill Winery and Vineyards. Hang your hat at a charming bed and breakfast or indulge in a spa treatment at the Salamander Resort and Spa. Complete your tastings and sightseeing at the Bluemont Winery, followed by a final stop at Hillsborough Winery. 

Begin at Stone Tower Winery

 On your first day, you'll drive along Route 15 to Stone Tower Winery. Along the way, you'll see The Oatlands Historic House and Gardens. If you enjoy learning about Virginia's history and seeing beautiful architecture, we recommend stopping by The Oatlands for a tour of the house and grounds. The Oatlands is home to the second-oldest propagation greenhouse in the country. 

Once you arrive at Stone Tower Winery, you'll enjoy beautiful views, delicious wines, and delectable dishes. Tasting rooms and tours of the inner workings of the vineyards are available to all. 


Stone Town Winery is located at 19925 Hogback Mountain Road, Leesburg, VA, 20175. The winery is open to visitors, with parties of 8 or more needing to make a reservation. Hours are from 11 am to 6 pm, Thursday through Monday.


Visit stone tower winery

Proceed to Cana Vineyards

 Your next stop is Cana Vineyards and Winery in Middleburg. If you're hungry, we recommend a stop at Gilbert's Corner located along Route 50 at the roundabout. There, you can purchase fresh produce at the Saturday farmer's market, or you can grab a barbecue lunch to go. As you continue on Route 50, you’ll travel through the Village of Aldie. If you're in the mood for something sweet, stop by the Little Apple Pastry Shop. For those who'd like a shopping break, we recommend locally owned Mercer Tavern Antiques. Once you arrive at Cana Vineyards and Winery, delight in visual reverie. You can walk among the fields, taste wine, and savor the region’s orange-lit sunsets. At Cana, you are welcome to bring snacks, or you can purchase the vineyard’s light fare. If you've brought your pups along for this trip, they are welcome at Cana too. 


Cana is located at 38600 John Mosby Highway, Middleburg, VA 20117. Hours are from 12 p.m. to 6 p.m. Thursday, Friday, Sunday, and Monday, 11 a.m. to 6 p.m. on Saturday, and the winery is closed Tuesday and Wednesday.


Visit Cana Vineyards

Time to relax

 After a day of indulging your senses in D.C.’s Wine Country, we recommend a relaxing night at one of the region’s many bed and breakfasts. Favorites include the Little River Inn, Goodstone Inn & Restaurant, and Stone Gables Bed & Breakfast. 

Visit our Hotel Guide

Loudoun Wine inspired Travel-- Day Two

Begin at Greenhill Winery & Vineyards

 We recommend that you begin your second day at Greenhill Winery and Vineyards, located at 23595 Winery Lane, Middleburg, VA 20117. This winery is open every day of the week from 12 pm to 6 pm for visitors and tourists alike. Guests will enjoy award-winning wines with a menu for all palettes while taking in beautiful views.  

Visit Greenhill

Proceed to Bluemont Winery

 Next, travel to the village of Bluemont for a stop at the Bluemont Winery, located at 187755 Foggy Bottom Road, Bluemont, VA 20135. The hours are from 11 a.m. to 5 p.m., Monday through Thursday, and 11 a.m. to 7 p.m., Friday through Sunday. A staple of Bluemont, wine tasters can enjoy scenic views while in the tasting rooms. Bluemont is known for its breathtaking views of the Blueridge Mountains.

Visit Bluemont

Enjoy the sunset at Hillsborough Winery, Brewery & Vineyard

 The last winery on this list is the Hillsborough Winery, Brewery, and Vineyard. This vineyard is located at 36716 Charles Town Pk, Hillsboro, VA 20132 and offers gorgeous views of rolling hills. A guest favorite is a flight of rose wines accompanied by live music.

VISIT Hillsborough

Additional Itineraries

If you'd like to continue exploring Loudoun, we've got more planned for you.

Explore Loudoun

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