A Weekend Roadtrip Through Beautiful Loudoun County


With leaves changing color and temperatures starting to drop, autumn is a perfect time to take a drive in scenic Loudoun County. With its rustic charm, beautiful views, great shopping, and wineries galore, it’s no surprise that D.C.’s friendly neighbor is an unforgettable escape. And wineries ‘galore’ is no tall tale: Loudon’s more than 40 wineries and tasting rooms give you an opportunity to experience one of the finest wine regions in the country. So if you don’t have time to fly to Napa or Sonoma, and appreciate a less commercial approach to wining, a weekend in northern Virginia is the ticket.

Not familiar with Loudon County? Located in the foothills of the Blue Ridge Mountains in Northern Virginia, just 25 miles west of Washington, D.C., Loudoun County is home to seven towns and 11 villages and communities. Dubbed as Northern Virginia’s premiere destination for wine lovers, Loudoun also boasts the LoCo Ale Trail, featuring 20 breweries and counting, for those who lean more towards suds over sipping wine. So when it was time to decide on a destination for a girls weekend trip, it was no brainer for us to pack up the Chevy Malibu, and hit the road just about an hour outside of Washington D.C. to the beautiful wine region of Loudon County.


Every good roadtrip starts with a playlist. And for our 1-hour drive, the decision was for 90s hits on the Malibu’s Sirium XM oldies station. After belting out oldies from SWV and Brandy, we arrive at the resort! The luxurious Salamander Resort & Spa in Middleburg is nothing short of breathtaking. And the best part about it is that we can take in everything that Virginia’s horse and wine country has to offer at this sprawling resort. The options are endless: Tour the vibrant fall foliage, taste local wines, gather around the fire pits, ride horses, and zip high above the beautiful Loudon property. And if you’re like us looking a unique experience, sign up for archery, or even seasonal cooking classes with Executive Pastry Chef Jason Reaves on Saturdays, and learn to how to make “Fall Harvest Sweets” using locally harvested ingredients including apples, pumpkins, and raspberries.


After breakfast, we spend the day shopping, wining and sipping. First things first, a visit to Virginia’s second smallest town, Hillsboro, is in order. Hillsboro, home to Hillsborough Vineyards, is a hillside estate run since 2003 by Turkish-born Bora Baki and his son Kerem. Hillsborough’s tasting room is housed in a renovated 1840s stone barn, a cool respite during the dog days of summer or a perfect autumn day. The terrace is a scenic spot to enjoy a glass wine, with views of the gardens and fountains, framing the valley below and the Blue Ridge Mountains in the distance.

From Hillsboro, we travel northwest to Breaux Vineyards, one of the state’s largest wineries with more than 100 acres of vineyard planted across their 404-acre estate. As we drive up, we follow a meandering driveway past manicured lawns that give way to sweeping views of vineyards leading up to Short Hill Mountain. Nestled between the hills, Breaux’s vineyard and mountain views can be enjoyed from the tasting room, Patio Madeleine, and their landscaped terraces. We then have lunch at Magnolias at the Mill, also in Purcellville, housed in a magnificently restored 1905 grain mill. The restaurant serves good brick oven pizza, entrée salads like the tasty grilled flank Caesar and a house made spinach cheese ravioli in a creamy mascarpone tomato sauce. Needless to say, after a day of wine-sipping (not to mention a light breakfast), we were starving and savored our Magnolias.

We end the day with one of the most impressive views in the county. Bluemont Vineyards sits high on an eastern slope of the Blue Ridge Mountains at 951′ above sea level, offering spectacular views of the countryside and beyond. It is spectacular, and offers picturesque falls views that are perfect for any fall wedding, or special occasion. It’s said that on a clear day, you can even see the Washington Monument from the tasting room. This low-key family winery offers live music most weekend days, with plenty of outdoor on the patio and in the grass. The most delicious option on the menu? The flavored wine slushies, and the cakes in a jar. And yes, we enjoy plenty of them.

For some retail therapy, Leesburg Corner Premium Outlets is just what the doctor ordered, with 110 swank brand name stores like Barneys New York Outlet, Coach and DKNY. Because, what would be a girls trip without a little shopping? Downtown Middleburg is more the ticket for indie shops and window browsing, as we literally continue to ‘shop ‘til we drop.’ After a visit to The Fun Shop, a multi-building department stores and gift shop and a local icon for more than 50 years, we decide to call it quits, and enjoy dinner at the Salamander’s Gold Cup restaurant.


Since we are fired up for our last day, we decide to rent bikes after breakfast and take a spin on the Washington & Old Dominion Railroad Regional Park, which is a 45 miles of paved trail that runs from Shirlington to Purcellville and was built on the former railroad bed of the W&OD Railroad. Though we don’t bike the whole trail, it’s beautiful to take a spin through Loudon on a beautiful fall day.

It’s now time to hit the water. We load in the Malibu and head 45 minutes to our next adventure: whitewater rafting at Harpers Ferry Adventure Center! The adventure center, located at the northern tip of Loudoun County, offers much more than rafting, such as tubing, zipline, aerial adventure park, jumping pillow, kayaking, canoeing, team building, fishing, hiking, and camping and cabin accommodations. What a blast! We manage to stay in the raft the entire time, and survive the waves of West Virginia.

From there, it’s time to continue our wine journey at Greenhill Winery & Vineyards. Greenhill opened in August 2013 and features 11 acres of vitis vinifera vineyards set against a stunning backdrop of the Blue Ridge Mountains.  The winery has been visited by the first lady and also had its sparkling featured in the gift bag given to select nominees at this year’s Academy Awards. Greenhill has plans to open a new production facility and a two-story, equestrian-themed, barn-style Tasting Room & Terrace, complete with outdoor seating, lounge eating and event space.
Following Greenhill, our final stop of the weekend is  50 West Vineyard. Started by the owners of Sunset Hills Vineyard, the vineyard uses 100% Virginia grapes grown at five farms located in Shenandoah and Loudoun counties . The tasting room is a converted stable with an open and contemporary feel.  It sits high on a bluff and offers stunning views of the Bull Run Mountain range.  The nearly 40-acre property includes a 1980s passive solar “Frank Lloyd Wright style” house that is being renovated into a wine clubhouse.

Kimberly Wilson

Kimberly Wilson

Kimberly is a NYC-based editor, writer and social media strategist. She also moonlights as the editor of Travel Noire.

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