When it comes to Virginia Wine Country, Charlottesville wineries are one of the east coast’s top destinations. The over 40 wineries along the Monticello Wine Trail—all within 25 miles of Charlottesville—are well known for their delicious wines, spectacular mountain views and gracious hospitality. Creating an even more unique wine experience, many wineries also offer special on-site wine classes and tours. Guests are welcome to explore gardens, participate in painting and cooking classes, join in a wine dinner, take a tour on horseback, partake in a wine class, or visit the cellar.
Charlottesville Named Wine Region of The Year
In 2023, the Charlottesville area’s Monticello Wine Trail won Wine Enthusiast’s prestigious Wine Region of the Year Award. The region was one of four finalists—and the only North American nominee—alongside the renowned winemaking regions of Lambrusco in Italy, Provence in France, Swartland in South Africa and Victoria in Australia. The judging for this award was based on a variety of criteria, such as trend-setting, brand vision and impact on consumers and trade in the wine world.
Representatives also noted that Charlottesville wineries in particular have proved vital to the success in tourism and job creation in the region. Along with the Wine Region of the Year, Barboursville Vineyards’ Luca Paschina was named one of five finalists for Winemaker of the Year worldwide. The recognition the region received in the competition was an important step in the story of the Virginia Wine Industry’s progression. Although Virginia’s wine story technically began back in the 1600s, it was the founding of Barboursville Vineyards in the 1970s that truly kick-started the wine industry as we know it today. The Monticello wine region in Charlottesville, Virginia, offers a picturesque landscape of rolling mountains paired with amazing wines that create a wonderful tasting experience for guests.
Gold Winning Charlottesville Wineries (North, Off Route 29 Corridor)
Barboursville Vineyards
(Barboursville, VA)
Barboursville Vineyards is a destination winery in every sense of the definition: it is a historical attraction, it is an award-winning winery and it has an award-winning restaurant and an award-winning inn onsite. the estate itself is a tourist attraction, home to the ruins of Governor James Barbour’s mansion, designed by his friend Thomas Jefferson. guest are encouraged to stroll around the Palladian style ruins, once one of Jefferson’s architectural masterpieces.
Since 1990, Italian winemaker Luca Paschina has helped Barboursville win the coveted Virginia Governor’s Cup five times, with several of its wines garnering top honors. The Discovery Tasting Room is open daily, while the stately Library 1821 is open Wednesday through Monday, presenting a changing selection of both current and older vintages with bit-sized culinary pairings. The Library is also the repository for historical documents such as the letter from President John Quincy Adams appointing James Barbour to his cabinet as Secretary of War, artifacts including original china donated by descendants of the Barbours family and of course, a collection of commendations for the estate’s wines.
Chestnut Oak Vineyard
(Barboursville, VA)
Janet Bolla, the winery’s owner, began the property as a retirement pastime that eventually evolved into a full-time job. Chestnut Oak Vineyard is located about 20 miles away from Charlottesville, Virginia. They cultivate and yield small lot white and red varietal wines. The terroir of Central Virginia is reflected in each of their wines, which are all barrel aged in oak or stainless steel tanks.
Their initial 2009 vintages were Cabernet Sauvignon and Petit Manseng, expanding to several more varietals from Chardonnay to Merlot. Experience wine by the flight, glass, or bottle at their tasting room, which officially opened in September of 2014. The tasting room is open Friday through Monday from 12 p.m. to 5 p.m. Cheese plates are available, or you may pack your own lunch.
The Barn at 678
(Barboursville, VA)
The vineyards at The Barn at 678 are the fruition of Ricky and Lorrie Bryant’s decades of agricultural and land management. Now as viticulturalists, they’ve created a family-run haven with stunning views of the vines and surrounding countryside.
The Barn at 678 delivers a tranquil, homelike feel with their comfortable hanging hammocks at the barn, cozy patio furniture throughout the grounds, and festive seasonal decor in the tasting room, greenhouse, and entertainment barn. With many flight options, guests are able to sample white and red wines, while also being able to mix and match seasonally crafted sangria, mulled wine, and cider. In addition to wine, the Barn at 678 serves hard ciders created and produced by Son of A Bear Ciders from Rapidan, VA. The Barn at 678 wines have earned recognition at the Virginia Governor’s Cup competition, taking home a gold medal for their 2021 Reserve Red along with silver medals for their 2019 Meritage, 2021 Petite Verdot, 2021 Viognier, 2022 Cabernet Franc, and 2022 Petit Manseng. With a new brewery license, their next adventure is to start crafting beer.
Horton Vineyards
(Gordonsville, VA)
Horton Vineyards in Gordonsville has been widely recognized as one of Virginia’s most innovative and influential wineries that contributed to the growth of the state’s wine industry. In 1983, Dennis and Sharon Horton planted a small vineyard at their home in Madison County. Inspired by a trip to the Rhone Valley, they planted Viognier grapes, as well as Virginia’s native grape Norton and several others. In 1993, the new Horton Cellars saw its first crush in its innovative stone underground cellars.
The winery’s Old World architecture with its stone turret is a nod to the Rhone Valley, where Horton was first inspired to try growing Viognier grapes in Virginia. The stunning vaulted tasting room and views of the Blue Ridge Mountains from the covered patio with its outdoor fireplace offer visitors two options for enjoying wine tastings and flights. Knowledgeable staff help guests explore their palates and choose wines that suit their particular tastes. The winery is owned and run by three generations of Horton women, with Dennis and Sharon’s granddaughter Caitlin taking over as winemaker.
Gold Winning Charlottesville Wineries (East, Near Keswick and Zion Crossroads)
Cunningham Creek Winery
(Palmyra, VA)
A family-run boutique winery, Cunningham Creek Winery is situated between Richmond and Charlottesville on the Monticello Trail. Their primary focus is award-winning French varietals and blends made in small lots. They’re great for picnics, families, and dogs. Savor the air-conditioned tasting room or the outside dining area. In addition, there is a fenced dog park where your dog can play while you sip on your wine. They have team trivia evenings once a month and live music every week.
You can schedule a private winery tour with the winemaker to discover more about the production of wine and to savor a unique wine sample. They provide classic tastings, glasses, bottles, and personalized wine flights. You can bring a picnic or choose from a variety of charcuterie boxes, cheeses, meats, and hummus at the farm store.
Southwest Mountains Vineyards
(Keswick, VA)
The newest vineyard and winery to open in the Monticello AVA is Southwest Mountains Vineyards in Keswick, VA. The Monticello AVA winery has 72 acres of vines under cultivation, with plans to expand to 100 acres. Paul and Diane Manning, two noted philanthropists and the founders of Southwest Mountains Vineyards, love horses, horse breeding and the culture of the community hunt—in their case, the Keswick Hunt Club. This love of horses and foxhunting in particular is evident in the equestrian décor.
You can schedule a private winery tour with the winemaker to discover more about the production of wine and to savor a unique wine sample. They provide classic tastings, glasses, bottles, and personalized wine flights. You can bring a picnic or choose from a variety of charcuterie boxes, cheeses, meats, and hummus at the farm store.
Gold Winning Charlottesville Wineries (West, Near Crozet & Afton)
King Family Vineyards
(Crozet, VA)
Founder David King originally bought the 327 acre Rosalind Farm in Crozet with the intention of building a polo filed. Though a vineyard was not part of the original plan, King became intrigued when a young man named Tom Vandenberg approached him in 1998 asking to lease 10 acres for winemaking. Curious to learn more, King hired a vineyard consultant and visited a nursery in California for inspiration.
After designing the winery on the back of a napkin and launching the full-fledged construction project, King Family Vineyards opened on October 1, 2002. Specializing in the production of premium wines that showcase the remarkable terroir and quality of the Monticello AVA, a list to King Family Vineyards is a unique experience with wines expressing the Virginia terroir. Summer weekend polo matches pair beautifully with winemaker Matthieu Finot‘s award-winning wines and an al fresco picnic. King Family Vineyards has won three Governor’s Cup awards with Finot at the helm, most recently in 2024.
Stinson Vineyards
(Crozet, VA)
Stinson Vineyards welcomes guests with sweeping panoramic views of the Blue Ridge Mountains. In 2015, the father/daughter team of Scott Stinson and Rachel Stinson Vrooman were joined by Rachel’s husband Nathan Vrooman, also of Ankida Vineyard. The family draws inspiration from the wines of the Bordeaux and the Loire Valley regions and the “garagiste” wineries of France.
You can see this influence in their winemaking and the winery, built into an old three-car garage. The relaxed tasting room and patio are the perfect spaces to enjoy a wine flight with light charcuterie. Guests may also bring a picnic. Gabrielle Rausse and Lucie Morton are top Virginia viticulturists and had a hand in the foundation of this 12-acre estate winery. In 2024, Stinson Vineyards won Gold Medals in the Virginia Governor’s Cup for their 2019 Meritage, 2021 Petit Verdot, 2021 Tannat, and 2022 Sauvignon Blanc, among other awards. Guests can enjoy tasting at the winery or extend a visit with a stay at the luxurious Stinson Vineyard Inn.
Valley Road Vineyards
(Afton, VA)
Located at the gateway to the scenic Rockfish Valley, Valley Road Vineyards is the first stop on the famed Nelson County 151 craft beverage corridor. The land offers optimal growing conditions for their estate-grown wines that include Sauvignon Blanc, Albarino, Rose, Merlot, Chardonnay, Viognier, Cabernet Franc and Petit Verdot.
From the very start, the vineyard’s wine received praise, earning a place in the prestigious Virginia Governor’s Cup case for their Gold Medal 2014 Petit Verdot. Many more recognitions have followed. Most recently they won second in the Monticello Cup for their 2023 Albariño. Guests can enjoy their wines in a variety of comfortable settings with Blue Ridge Mountain views, indoors and out: the rustic chic Tasting Room, on the Patio or covered Pavilion as well as in the shady Grove near the farmhouse. The winery offers locally sourced charcuterie and small pizzas from the local favorite, Sal’s. Guests are also welcome to bring a picnic. Live music, lawn games, talented staff and seasonal drinks like Frosé and mulled wine ensure each visit to Valley Roads Vineyard is special. The property welcomes weddings and events. Groups of 8 or more require a reservation.
Veritas Vineyards & Winery
(Afton, VA)
Veritas Winery’s simple white farmhouse and outbuildings surrounded by verdant vineyards paint the quintessential picture of Virginia country life. The winery is a combination of Southern hospitality and European charm with wines inspired by the Loire Valley, a lovely tasting room and patio, farm-to-fork dinning and unique accoummodations.
When owners Andrew and Patricia Hodson met and fell in love in Nottingham, England, little did they know that one day they would create an award-winning winery and family business in Virginia. But in 1999 they purchased Saddleback Farm and by 2001, their first vintage was ready for production. Their children followed them into the business, with their eldest daughter Emily as head winemaker. The Tasting Room offers reserved seating and tableside service inside or on the covered veranda with a menu including salads, sandwiches, charcuterie, cheese boards and sourdough toasts. The Veritas Food and Wine Experience features expert guidance from wine educators to walk guests through five wine and food pairings. If you prefer to do your sipping outdoors, reservations are not required for The Lawn or The Grove—bring your own blanket or chair—or The Bricks, where you can order wine at the bar for your table. Guests may bring their own picnics in these areas.
Gold Winning Charlottesville Wineries (South, Route 20)
Eastwood Farm and Winery
(Charlottesville, VA)
Eastwood Farm and Winery is just five miles from the Downtown Mall in Charlottesville, but offers a true escape on its 77 acres with multiple indoor and outdoor spaces, hiking trails, a variety of food options and, of course, wine. Eastwood Winery is a women-owned and family-operated farm winery that began production in 2018. The property sits on the west side of Carters Mountain Ridge on the site of a historic farm. Their award-winning Orchard blend is a fruit wine made entirely from apples and pears.
Eastwood Winery stretches into the mountains with a stunning overlook point and is filled with orchards, meadows and forests. You can drive or hike to the mountaintop overlook for a picnic or a special yoga session or enjoy fire-grilled snacks from the food truck parked by the Tent & Terrace Bar, which features picnic tables and Adirondack chairs. The Barn and covered Veranda are open year-round for enjoying award-winning wines, ciders, beer and shareable small plates. The menu even features a tasting flight of chocolate from local chocolatier, Gearhart’s Fine Chocolates.
Michael Shaps Wineworks
(Charlottesville, VA)
Michael Shaps Wineworks is a prominent winery and custom crush facility known for producing high-quality wines and offering winemaking services to other vineyards and wineries. Michael Shaps, who originally trained in Burgundy, France, is a highly regarded winemaker with extensive experience in both Old and New World winemaking techniques He established Michael Shaps Wineworks in 2007 in Virginia, recognizing the region’s potential for producing premium wines.
Michael Shaps Wineworks operated out of a modern facility equipped with state-of-the-art winemaking equipment. Shaps focuses on crafting wines that reflect the unique terroir of Virginia. He combines traditional winemaking practices with innovative techniques to produce wines that are expressive, balanced and age-worthy. The winery produces a diverse portfolio of wines, from single varietals to blends and special cuvées that highlight the best characteristics of Virginia grapes. In addition to producing their own wines, Michael Shaps Wineworks provides custom crush services for other wineries and vineyards. This allows smaller producers to access Shaps’ expertise and facilities to create their own wines under their label. Their connections with winemakers in France, as well as many local chefs and winemakers, allow them to collaborate on beautiful events. The winery has a tasting room where visitors can sample a selection of wines and learn about the winemaking process. It offers a relaxed atmosphere where guests can enjoy views of the vineyards while tasting wines produced on-site.
Notable Wineries Near Charlottesville
There are many excellent award-winning wineries near Charlottesville even outside of the Monticello Wine Trail. Some of our favorites include: Castle Hill Cider, Early Mountain Vineyards, Prince Michel Winery and Vineyard, Fifty-Third Winery and Vineyard, Ankida Ridge Vineyards
The History of Charlottesville’s Award-Winning Monticello Wine Trail
It was the establishment of Barboursville Vineyards in 1976 by Italy’s venerated wine family, the Zonins, that kickstarted the growth of the wine industry in Virginia, as well as in the Monticello region, which officially became an American Viticultural Area (AVA) in 1984. And with the burgeoning growth of the Monticello AVA and Virginia’s wine industry came the growth of wineries as tourism destinations and thus the Monticello Wine Trail—a collection of wineries known for producing exceptional wines that are acclaimed nationally and internationally—was created. In the annual Virginia Governor’s Cup Competition, wineries from the Monticello Wine Trail regularly dominate the Governor’s Cup Case–the top 12 wines of the competition–and in the past 10 years, six Governor’s Cup winners were Monticello AVA wines.
While adventuring along the trail, oenophiles can also experience some of America’s oldest history with visits to presidential homes like Monticello, Montpelier and Ash-Lawn Highland. Learn more about how winemaking began here with our popular reference feature, “Virginia’s Great American Wine Story.” Tasting the unique terroir in the award-winning wines that hail from the Monticello Wine Trail is a must for any wine lover. You’ll surely leave satisfied in the knowledge that you’ve experienced the absolute best of Virginia Wine Country. ~
Visiting The Monticello Wine Trail
When visiting the Monticello Wine Trail, be sure to read up on all of the local resources on WineandCountryLife.com. You’ll learn from the local experts about local wineries with fine dining, Virginia wineries with overnight accommodations, which wineries to visit for spectacular fall views, museums and attractions, or for a cozy winter tasting experience, the top wine festivals in Virginia, and all of the newly opened Virginia wineries. On the Monticello Wine Trail website, visitors will also find several helpful resources, including maps an itinerary planning tools.
More Charlottesville-Area Wineries on the Monticello Wine Trail
Afton Mountain Vineyards<
Blenheim Vineyards
Burnley Vineyards
Cardinal Point Vineyard & Winery
Chisholm Vineyards
Chiswell Farm & Winery
Flying Fox Vineyard
Gabrielle Rausse Winery
Glass House Winery
Grace Estate Winery
Hardware Hills Winery
Hark Vineyards
Hazy Mountain Vineyards
Jefferson Vineyards
Keswick Vineyards
Knights Gambit Vineyard
Loving Cup Vineyard & Winery
Lovingston Winery
Merrie Mill Farm & Vineyard
Montifalco Vineyard
Moss Vineyards
Mountain & Vine Vineyards and Vineyards
Pollak Vineyards
Pippin Hill Farm & Winery
Reynard Florence Vineyard
Septenary Winery
Stinson Vineyards
The Barn at 678 Vineyard
Trump Winery
Valley Road Vineyards
Wisdom Oak Winery
Woodbrook Farm Vineyard
