Virginia Wine Month: A Journey Through The Mosby Cluster

By Chelsea Rose Moore | Photos by Michelle Baker

The 31st annual Virginia Wine Month kicks off in just a few weeks. The region showcases spectacular fall colors and one of wine lovers’ favorite celebrations in October. Loudoun is home to more than 40 wineries, each a unique destination offering boutique-style wine and boasting of stunning views. 

With that many wineries and tasting rooms, you may not know where to begin when you visit Loudoun County. To make it easier, Visit Loudoun has grouped Loudoun’s wineries into six wine clusters, each uniquely its own. Featured on the cover of this issue is part of the Mosby Cluster, located in the Middleburg American Viticulture Area.  The wineries in this cluster sit primarily along Route 50, John Mosby Highway, as it travels through the towns of Aldie and Middleburg. Here, wine and horse country intersect. What better way to celebrate Virginia wine and live the Middleburg life than by taking a tour.

2042 Burrland Lane Middleburg, Virginia 20117

Boxwood Estate Winery has made significant headlines in Virginia’s wine industry. According to the website, the Middleburg AVA (American Viticultural Area) in Virginia is home to 200 square miles in Loudoun and Fauquier Counties, and in 2012 was the seventh AVA established in Virginia. Boxwood Winery initiated the six-year petition process to establish Middleburg as an AVA in 2006. Today, the Middleburg AVA includes over two dozen wineries and vineyards.

Boxwood Estate Winery is the fruition of a dream of John Kent Cooke, the former owner and president of the NFL Washington Redskins. As a longtime wine aficionado and collector of French wines, he wanted to make Virginia Bordeaux-style wines steeped in Virginia’s terroir. He hired renowned wine consultant Stèphane Derenoncourt, a winemaker and consultant to over 90 wineries across the globe, in addition to a team of internationally acclaimed staff. Together, they helped make Boxwood the success it is today.

Signature wines include Trellis and Topiary, the former a blend of merlot, cabernet franc, cabernet sauvignon, and petit verdot. Topiary is a blend of merlot, cabernet franc, and petit verdot. They also make an incredibly popular sauvignon blanc and rosé.

38600 John Mosby Highway Middleburg, Virginia 20117

What do cornhole, hula hoops, board games, and wine all have in common? Simple: Cana Vineyards & Winery. Cana was awarded “Loudoun County Winery of the Year” from the New York International Wine Competition four years in a row (2016-2019).

Filled with award-winning wines and stunning views of the Bull Run and Blue Ridge Mountains, the team at Cana is focused on creating a space to bring people together. Cana’s winemaker Melanie Natoli won “Winemaker of the Year” at the Women’s International Wine Competition in 2017.

Owners Bryce and Lisa Petty purchased the winery from the Bell family in October 2018, and together with longtime friends and co-owners Tom and Michelle Grant, they are working on infusing the property with new energy. Most recently, they opened a “Sunset Pavilion” in June, a covered outdoor space for guests to enjoy their wine and connect with friends and family. “I love seeing how much of a great time people are having,” said Lisa, “It’s heartwarming to know that we helped foster that.” Have a four-legged friend? Stop by Cana’s new Bark Bar in the main building to pick up treats and water for your furry friend.

39025 John Mosby Highway Middleburg, Virginia 20117

Welcome to the Ag District. Owner Jennifer McCloud opened Chrysalis in 1998. She’s been a longtime wine enthusiast and a pioneer in Virginia’s wine industry. Years ago, she came to Virginia to “grow Norton and be involved in the restoration of this grape that had been renowned in Virginia and then died out during prohibition.” Today, she said, Chrysalis is the top producer of Norton in the world. Her goal was to “put viognier on the map,” which she did while helping pave the way for viognier to become Virginia’s signature white grape.

The wine industry is a combination of nature, science, art, and people. “It’s got nature, seeing the beauty of the spring, when all the new growth happens. And the bounty of the harvest at the end,” McCloud said. “It’s got science, with the transformation of the grapes into wine and malolactic fermentation. It’s got the beauty of the countryside. And, of course, the experience of drinking really good wine. You wrap that all up, and it’s the people, the interaction with people who are so excited to be drinking your wine and eating your food.”

Chrysalis is more than just a winery. It’s an agricultural district and a harkening back to Loudoun’s farming heritage. “We’re trying to restore the historic connection of agricultural here,” McCloud said. The property is home to Devon cows, a creamery producing artisan cheeses, and a bakery.

39060 John Mosby Highway Middleburg, Virginia 20117

50 West Vineyards is named after the historic road it is located next to. At over 3,000 miles long, Route 50 runs from east to west coast. As their website touts, 50 West is “American-made wine on an American Highway,” a symbolic hats-off to the history of the road and the stories it carries.

One of the largest vineyards in Virginia, 50 West grows fruit on five farms in Northern Virginia and has 75 acres under vine. Their flagship wine is Aldie Heights Cuvee, a blend of tannat, petit verdot, cabernet franc and merlot. The current 2015 vintage won gold at the 2019 Virginia Governor’s Cup.

The team at 50 West is focused on educating their guests about wine. “Most of our staff are wine certified through the Court of Sommeliers or the Wine & Spirit Education Trust,” said Retail Operations Manager Bridgette Smith, “We also lead weekly staff education about wines of 50 West, Virginia, and the world. With this level of education, we aim to create an experience unlike most Virginia wineries.”

This unique experience is proving to be memorable for guests. “Most of our club members and ‘regulars’ jokingly call us their ‘cheers’ because our tasting associates are very personable and remember their names and their favorite wines,” said Smith, “We attempt to create a friends and family vibe at the winery, where everyone who walks through our doors knows this is their neighborhood winery.”

23075 Evergreen Mills Road Leesburg, Virginia 20175  

Sophistication and elegance meet rustic Virginia vibes at Loudoun’s newcomer Fleetwood Farm Winery. An adults-only winery, Fleetwood is dedicated to educating guests about wine.  

The winery offers a 90-minute history tour of their historic manor house. Learn about the notable figures associated with the property, including George Washington, John Hancock, and Fairfax County’s first sheriff. The tour wouldn’t be complete without a wine tasting for guests. Find more details on the history tour at Fleetwood’s website.  

With live music every weekend and regularly scheduled food trucks, guests can choose to do a tasting in the tasting room or a private wine tasting in the historic manor house. Order flatbread pizza, a charcuterie board, or a hummus plate to accompany your glass. Fleetwood wines include a riesling, petit manseng, chardonnay, cabernet sauvignon, and a 2017 Meritage blend. The winery celebrates happy hour every Thursday from 2-7 p.m. – grab a glass for $7.  

23595 Winery Lane Middleburg, Virginia 20117

Filled with rolling hills, Charolais cattle grazing in the fields, and a beautiful tasting room, your journey to Greenhill will make you wonder if you’ve somehow been transported to another world. From the truly inspired décor to the outstanding wines, no detail has been missed here.

During your visit, you may be lucky enough to see horses traveling through the fields, while riders stop for a celebratory class of Blanc de Blancs, the sparkling wine that was included in the 2016 Academy Award “swag bags” given to Oscar nominees.

With award-winning wines and signature red blends named after philosophical concepts, prepare for an elevated experience and leave with a deeper appreciation for the equestrian culture. While you’re here, don’t miss a peek at the stunning Barrel Room. Take home some Charolais beef, honey from Greenhill’s apiary, and an assortment of other gourmet food items. Starting Sunday, Sept. 8, Greenhill is hosting a twice monthly fall farm market, featuring seasonal items and produce from Shenandoah Seasonal.

22860 James Monroe Highway Aldie, Virginia 20105

The name “Quattro Goombas” is Italian for “four close friends,” an expression that captures the heart of the Quattro Goombas’ experience. Here, family and friends are celebrated, and old-world tradition is king. With both a winery and a brewery onsite, Quattro Goombas offers a little something for everyone.

The wine bar is home to Quattro, the winery’s pizza shop. With square-cut, Sicilian-style slices, the pizza is modeled after the owner’s hometown shop in Western Pennsylvania. The Quattro team bakes fresh baguettes daily and offers a full selection of cheeses to spread on top of your warm bread. Order one of the popular wine slushies and take in the beautiful fall weather.

By Visit Loudoun

  • Chardonnay: A medium to full-bodied dry white wine with fruit characters of citrus, apples, pear, or tropical.
  • Cabernet Franc: A medium bodied red wine known for its spiciness and herbal characters.
  • Norton: A native Virginia grape that is dark in color and its fruity flavors may include plums and tart cherries.
  • Viognier: The signature wine grape for Virginia has more natural aromatics compared to Chardonnay including notes of peach, pears, violets.
  • Blends: The art of the winemaker is often shown in a blend of different grapes just as a chef would use different spices. Ask about the grapes used when tasting these special wines.
  • Other varieties: Cabernet Sauvignon, Chambourcin, Merlot, Malbec, Petit Verdot, Riesling, Tanat, Traminette, White Bordeaux. To learn more about D.C.’s Wine Country, go to

Your journey through the Mosby Wine Cluster doesn’t have to be self-led. Consider booking a wine tour to maximize your experience. If you’re not sure where to start, check out the resources available through Visit Loudoun. With lists and details on the area’s wineries and wine tours, this will serve as a great starting point!


Want a VIP experience through Loudoun’s wine country? At DiVine Wine Tours, every guest is a VIP and every wine tour has special elements to make your day as memorable as possible. Each tour visits three wineries in a specific wine cluster, allowing guests to spend up to two hours at each winery. DiVine is an all-inclusive wine tour company, which means they make all your plans and reservations. Guests will enjoy elevated tastings, a visit with the winemaker or owners, and lunch.

The drivers introduce guests to the region’s history by sharing facts about Virginia wine and the area itself. They take professional photos of each group as well, sending guests a file of edited photos to enjoy for years to come. “Each Loudoun County cluster is absolutely gorgeous in its own way,” said DiVine Wine Tours owner Amy Denton. “There’s something about the Mosby Cluster that is so classic Virginia. It has that horse country element to it that the other clusters don’t have. It’s so clean and beautiful. It’s such a unique experience and it’s so Loudoun County. For people coming from D.C., it probably feels like a world apart. It’s a great way to show what Loudoun County has to offer.” ML

This article first appeared in the September 2019 issue of Middleburg Life.

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