The fall is a perfect time to plan a visit to Virginia Wine country. Ken and the KWG Tasting Panel have been covering the winning wines from the Virginia Governor’s Cup for years. Recently, our coverage has expanded beyond just the Governor’s Cup winners. Ken has been so impressed with Virginia wines that Theresa and he visited some wineries in the Charlottesville region in October of 2024. We highly recommend that you check out the six Virginia wineries in this post. We will start from the south near Charlottesville in the Monticello AVA and make our way north.
Our first stop back in 2024 was at Blenheim Vineyards, so I thought it would be a great place for you to start. It is a family-owned winery in Charlottesville. It was founded in 2000 by owner and well-known musician Dave Matthews. Blenheim was created with a focus on producing approachable, expressive wines that reflect Virginia and the vineyard itself. The winery sits on a historic property just south of Charlottesville, surrounded by rolling vineyards and views of the Virginia countryside.
During our visit, we sat down with Winemaker and General Manager Kirsty Harmon who has led Blenheim’s winemaking program since 2008. Today, the estate includes approximately 20 acres of vines farmed with an emphasis on sustainability and thoughtful stewardship of the land. Blenheim produces wines entirely from Virginia-grown fruit, including Cabernet Franc, Chardonnay, Sauvignon Blanc, Alberino, Viognier, distinctive blends, and a traditional-method sparkling wine. Blenheim is also a founding member of the Wine Atlas Collective, a collaboration of eight independent wineries from leading wine regions across the country, connecting their wine club communities through reciprocal benefits and shared experiences.
The Blenheim tasting room was designed by Dave Matthews and master craftsman William Johnson. It offers a unique view into the winemaking process, with glass-paneled floors looking directly into the working wine cellar below. Outside, a large tent and expansive grounds overlook the vineyard, creating a relaxed setting for tasting flights, bottles, and seasonal events. From harvest happening beneath the tasting room to art exhibitions and live music overlooking the vines, you’re bound to be entertained throughout your visit to the winery. Guided tastings of five wines are available for $25 per person. Tastings last about an hour and are led by the Blenheim team, who’ll walk you through each wine and the stories behind them. For indoor tastings, they recommend making a reservation, especially on weekends, and outdoor spaces are first come, first served. With that said, they welcome walk-ins when space allows. Here is a link to the KWG Blenheim webpage, with all our wine recommendations.
Our next stop is the Trump Winery which is 10 minutes and just 3 miles from Blenheim. It sits on nearly 1,300 acres in the foothills of the Blue Ridge Mountains, a few miles from Thomas Jefferson’s Monticello in Virginia’s Monticello AVA. The region Jefferson himself staked as the future of American wine. With 200 acres under vine, it is the largest vineyard in Virginia. The first blocks were planted between 1999 and 2007 and they range from roughly 600 to 1,200 feet in elevation on predominantly south-facing slopes. Air drainage and long afternoon exposure give the fruit hang time while preserving the natural acidity that defines the estate’s style. Redevelopment and new planting have been continuous since 2011.
During our visit we met with and tasted wines with the Director of Winemaking Jonathan Wheeler. Jonathan has worked these vineyards since 2006. A Finger Lakes native with prior harvests in Sonoma, Monterey, and Marlborough, Wheeler oversees the wine and cider programs from a 50,000-square-foot production facility with 100,000 gallons of tank capacity and an underground barrel cave. The sparkling wines are made in the traditional méthode champenoise with extended tirage, and they are the estate’s calling card. The reds are Bordeaux-variety blends and single varietals aged in French oak. The addition of the cidery production started in 2022 with the planting of 6,000 apple trees and the first production of ciders released in 2024.
Trump Winery is also a destination. The Grand Hall Tasting Room pours sparkling, white, red, and taster’s-choice flights with a seasonal kitchen menu and vineyard views from an outdoor terrace, with reserve tastings offered on select Saturdays. Overnight guests can stay at Albemarle Estate, the restored manor house on the property, and the estate cidery presses fruit from its own orchard, and pick-your-own apples each fall. All of it sits on the Monticello Wine Trail within a short drive of Charlottesville, Monticello, and Highland.
Here is a link to the KWG Trump Winery webpage, with all our wine recommendations.
Our next stop heading north is Jefferson Vineyards. It is a historic winery located in Charlottesville, Virginia, situated at the foot of the Blue Ridge Mountains just steps from Monticello. The site is home to some of the earliest commercial winemaking in the region, beginning with Thomas Jefferson’s deep interest in wine and his efforts to promote viticulture in Virginia alongside the Italian vintner Philip Mazzei. More than 200 years later, their vision became a reality at Jefferson Vineyards.
Today, the winery carries on Jefferson’s legacy with a deep commitment to quality and a profound sense of place, earning consistent recognition at some of the country’s most prestigious competitions. From its highly recognized Viognier to its celebrated Meritage, Jefferson Vineyards remains dedicated to crafting wines that reflect the unique character of this remarkable corner of Virginia. Their head winemaker since 2013 is Christopher Ritzcovan.
The winery is open seven days a week, offering wine by the flight, bottle, or glass, with live music on the weekends. Guests are welcome to enjoy a range of outdoor seating and take in the views of Carter’s Mountain. For more information and to plan a visit, check out their plan a visit page.
Our next stop is at Keswick Vineyards just off Route 231 at 1575 Keswick Winery Drive in Keswick, Virginia. The Schornberg family has owned Keswick Vineyards since 1999, relocating from Michigan to raise their kids and realize their dream of owning and operating a winery. The first vines were planted in the year of 2000, and the first vintage from those estate grown grapes was made in 2002. They currently farm 60 acres, primarily of Vitis Vinifera, producing wines that reflect the land and environment where they are grown.
Their winemaker is Stephen Barnard, who hails from South Africa and is married to their daughter Kath. As he puts it, “I have made every mistake that could possibly be made.” He is a winemaker who favors minimalism over intervention, and restraint and elegance over brashness and boldness, and he loves challenging the conventions of normalcy. Keswick Wines are often age-worthy but always made with intentional precision, and they have gained some noteworthy accolades in the past.
The farm also hosts weddings and focuses on the customer experience. You can also take a guided tour through their wine selections or build your own flight of four wines. Relax in the idyllic setting and enjoy your wine at your own pace at their multiple indoor and outdoor bars, courtyard tables, or scenic picnic areas. There are also food trucks and live music every weekend. Finally, they even offer miniature golf on site. Tickets for mini golf can be purchased in the Tasting Room. Keswick is fully committed to promoting and growing the reputation of Virginia wine. Stop on by and see for yourself!
As we continue our trip north on Route 231, head over to Route 33 to discover the Horton Vineyards at 6399 Spotswood Trail in Gordonsville, Virgina. Horton is a three-generational winery led by remarkable women. Their founder, Sharon Horton, continues to oversee the vineyard operations she began decades ago. Shannon Horton, the second generation, bridges the vineyard and the winery, ensuring the seamless connection between harvest and production. Caitlin Horton, the winemaker, crafts exceptional vintages from the very grapes her grandmother nurtured, honoring the family’s legacy with every bottle.
Located in the scenic landscape of Orange County, Horton Vineyards blends tradition with innovation, offering a wide range of wines that showcase the unique terroir of Virginia. The vineyard’s commitment to quality and creativity has earned it numerous accolades, making it a must-visit destination for wine enthusiasts seeking a blend of heritage, craftsmanship, and bold flavors. Whether sipping a signature Viognier or exploring their award-winning blends, visitors to Horton Vineyards are treated to an unforgettable experience that reflects the passion and expertise behind every bottle.
Horton Vineyards continues to explore with new varietals and techniques to achieve the very best that Virginia viticulture can produce. The wine selection contains over 40 wines. Their knowledgeable staff will help you choose the wines for your self-guided tasting.
Our last stop is a Barboursville Vineyards. Less than 10 minutes away from Horton. They are celebrating their 50th anniversary in 2026. Barboursville is one of the founding estates of modern Virginia wine and a destination where wine, history, and Italian heritage converge. Founded in 1976 by Italy’s Zonin family, Barboursville lies in the rolling Virginia Piedmont between Thomas Jefferson’s Monticello and James Madison’s Montpelier. The estate surrounds the evocative ruins of the mansion Thomas Jefferson designed for Virginia Governor James Barbour, offering visitors nearly two centuries of American history alongside five decades of pioneering Virginia viticulture. In the year of America’s 250th birthday and Barboursville’s 50th, there may be no better time to experience this uniquely Virginian estate.
Today, Barboursville farms approximately 176 acres of vineyards within a nearly 900-acre estate, producing European varieties particularly suited to Virginia’s climate and soils. Its Italian roots are expressed through Vermentino, Nebbiolo, Fiano and Barbera, alongside Cabernet Franc, Viognier and the estate’s flagship Bordeaux-style blend, Octagon. Multiple Virginia Governor’s Cup honors and growing national recognition have helped establish Barboursville among Virginia’s most celebrated wineries.
Barboursville is designed for travelers who want wine to be part of a larger culinary and cultural getaway rather than simply a tasting-room stop. In 2026, Wine Enthusiast named the Palladio Restaurant one of its Best Winery Restaurants in the World, one of just 57 destination winery restaurants recognized globally, celebrating its Italian heritage, estate-grown ingredients and the connection between Virginia wine and the table. Guests can also explore library wines at Library 1821, walk the Jefferson-designed ruins, and extend their stay at the historic 1804 Inn and Cottages, surrounded by vineyards and countryside. Together, the wine, Palladio’s cuisine, history, accommodations, events, and Italian hospitality offer a remarkably complete expression of Virginia wine country. A place to taste, dine, explore, and stay. Finally, here is a link to the KWG Barboursville Vineyards webpage, with all our Barboursville wine recommendations.
From Blenheim to Barboursville, and all the stops in between—the wineries are just over an hour apart, making it easy to experience several destinations in one trip. Consider visiting three wineries each day and staying overnight in the area to fully enjoy the journey. It’s a perfect way to explore the diversity of Virginia wines while taking in the beauty, character, and hospitality of Virginia wine country.
This post was sponsored by the wineries and Virginia Wine.