20+ Award-Winning Wineries On the Monticello Wine Trail in Charlottesville & Albemarle County, Virginia

By: TLP's Partners

The Charlottesville region was just named Wine Enthusiast’s 2023 Wine Region of the Year – and for good reason! Charlottesville and Albemarle County have 40+ wineries along the acclaimed Monticello Wine Trail, and many of them are producing award-winning wines that are making wine aficionados from around the world take note. The 21 wineries listed here have won gold medals at the state’s premiere wine competition, the Virginia Governor’s Cup, and collectively, wineries on the Monticello Wine Trail received nearly half of all the gold medals awarded in 2023. Discover more about each award-winning winery and utilize the map feature to start planning your ultimate winter winery vacation!

Eastwood Farm and Winery

New to the Charlottesville winery scene, Eastwood Farm and Winery opened in 2020, and the woman-owned winery is already producing gold medal-winning wines. Visiting their property offers tasting options galore including multiple indoor and outdoor spaces to sip their delicious vintages (along with house-made craft beer and cider), plus hiking trails and an on-site food truck. You’ll want to stay all day!

eastwood wines from Monticello Wine Trail
Image Courtesy of Eastwood Farm and Winery

Cunningham Creek Winery

Family-owned and -operated, Cunningham Creek Winery welcomes everyone—kids and pets included! Enjoy award-winning wines while watching your dog run off-leash in the dog park, or relax with some wine and a picnic. Light snacks are available for purchase in the tasting room, and be sure to check the event page for live music, food trucks, and trivia.

Jefferson Vineyards

Purveyors of fine Virginia wines for more than 40 years, Jefferson Vineyards is a Charlottesville-area staple. The locale sits on the very same site where Thomas Jefferson and Filippo Mazzei began the first commercial vineyard in Virginia, an event pre-dating the Revolutionary War. Jefferson Vineyards has since bridged its traditions with modern viticulture practices to realize a dream nearly 250 years in the making.

Grace Estate Wines from Monticello Wine Trail
Image Courtesy of Grace Estate Winery

Grace Estate Winery

Focusing on agricultural tradition, Grace Estate Winery creates 100-percent estate grown Virginia wines at their 450-acre Mount Juliet Farm, winery, and tasting room. You may be sensing a theme: Virginia wine tasting experiences go hand in hand with breathtaking views, and Grace Estate is no exception. Plan to pack a picnic, and enjoy a lovely afternoon sipping award-winning wines and snapping some selfies throughout your experience.

Trump Winery

Planted with 227 acres of French vinifera varieties, Trump Winery is not only Virginia’s largest vineyard, but also the largest vinifera vineyard on the East Coast. A breathtaking 1,300-acre estate with an incredible vantage point which overlooks the beautiful rolling hills of the Charlottesville countryside. Enjoy wines by the bottle, glass, and flight, or enhance your visit by making a table reservation and pairing your selected varietals with artisanal menu items.

Afton Mountain Vineyards

Who wouldn’t want to sip award-winning wines in an all-weather glass pavilion while gazing at the Blue Ridge Mountains? Afton Mountain Vineyards’ vines were planted 45 years ago, making theirs some of the oldest in the state. Elevated at 1,000 feet on the eastern slope of Afton Mountain, the unique positioning of the vineyard allows grapes to thrive. And thrive they have, under the direction of winemaker Damien Blanchon, who has been at the helm for Afton since 2011.

CACVB Spring King Family Shoot SS
King Family Vineyards

King Family Vineyards

Stewards of the land since 1998, King Family Vineyards is a family-owned and -operated winery now producing 10,000 cases per year. Classic and reserved tastings as well as vineyard tours are all options to gain a deeper understanding of the King Family wine program. If you’re visiting late spring through early fall, Sunday Polo at King Family is a tradition not to be missed.

Pollak Vineyards

All of Pollak Vineyards’ wines are fully estate grown from their 34 acres of French vinifera, which is all harvested by hand. Small batch, big flavor, and high quality is what you’ll find at Pollak. Cozy up by the fireplace in the tasting room on chilly days or bring a blanket and picnic near the pond during warm ones.

Stinson Vineyards

Inspired by garagiste winemaking in France, Stinson is unique in both its technique as well as its design: a renovated three-car garage designed by owner and architect Scott Stinson. Winemaking team Rachel Stinson Vrooman and Nathan Vrooman focus on European-style wine styles that emphasize subtlety and complexity. Enjoy a glass or bottle from the garage, featuring 360-degree mountain and vineyard views.

Stinson Vineyards from Monticello Wine Trail
Inn at Stinson Vineyards, Image Courtesy of Virginia Tourism

Veritas Vineyard and Winery

Winemaker Emily Hodson’s philosophy is simple: allow the wine to show the beauty of where the grapes were grown, as well as a naturally balanced expression of the fruit by focusing on attention to detail and cultural practices. Hodson is one of just a few woman winemakers along the Monticello Wine trail who got her start in the Virginia wine industry and she has been at the helm for 15 harvests at Veritas. Plan a visit to enjoy these special varietals through a variety of experiences including tastings, food and wine pairings, picnics, and so much more.

Mountain & Vine Vineyards and Winery

Celebrate with Mountain & Vine Vineyards and Winery (Formerly Delfosse Vineyards and Winery) on winning the 2023 Governor’s Cup! Hugged between the hills in Faber, Virginia along the Monticello Wine Trail, Mountain & Vine Vineyards and Winery enjoys the elevation to guarantee both flavorful wine and fabulous views. Tour their terraced vineyards (one of the only in Virginia), pack a picnic, or make a weekend of it when you book a stay in their 100-plus-year-old Historic Chestnut Log Cabin, a peaceful respite overlooking the lake.

Albemarle CiderWorks from Monticello Wine Trail
Image Courtesy of Albemarle CiderWorks

Albemarle CiderWorks

A testimony to the enduring appeal and viability of family farms and innovative agricultural enterprise, Albemarle CiderWorks is first and foremost a nursery, cultivating more than 250 apple varieties to curate their library of Virginia hard ciders. In addition to sustainability endeavors, Albemarle CiderWorks won best in show for cider at the 2023 Virginia Governor’s Cup. Reservations are encouraged for parties of any size wishing to visit Albemarle CiderWorks. Guided tastings are available in addition to ciders by the glass, flight, and bottle.

Michael Shaps Wineworks

By 1995, Michael Shaps had accumulated numerous awards and acquired a reputation as one of Virginia’s up-and-coming winemakers. Now, nearly 20 years later, Shaps continues to be a leader in Virginia wine as both an innovator and entrepreneur. Shaps offers two tasting room experiences. 1650 Harris Creek Road features indoor and expansive outdoor seating and offers traditional tastings of the Michael Shaps Virginia wines, as well as the Maison Shaps Burgundy wines, imported from Shaps’ winery in Meursault, France. Rustic and industrial, the Wineworks Extended tasting room is attached to the working warehouse and offers everyday drinking wines in the Wineworks label, including flights, wine on tap, growlers, carafes, and bottles.

Castle Hill Cider

Founded in 2010, Castle Hill Cider was born after its owners decided to take Castle Hill back to its orchard roots. Colonel Thomas Walker, the original owner of Castle Hill Estate—and Thomas Jefferson’s legal guardian—was the first to bring Newtown Pippin apple scions to Central Virginia following his return from the Battle of Brandywine in 1777. The variety was planted at Castle Hill and became known as the Albemarle Pippin apple. Today, the estate boasts some 5,000 cider apple trees growing 40-plus varieties. Cidermaker Don Whitaker aims to tell the tale of the terroir and history of the landscape in each glass of Castle Hill Cider. 

Nestled on 600 acres of rolling Virginia countryside is a stunning barn, which is home to the tasting room, production operation, and serves as a private event venue. Patio seating as well as groupings of Adirondack chairs dot the landscape while soft seating is available indoors. Hard cider by the glass, bottle, and flight is available as well as innovative cider cocktails and a light bites menu.

Pippin Hill Eric Kelley
Pippin Hill Farm & Vineyards

Pippin Hill Farm & Vineyards

A culinary vineyard, Pippin Hill’s focus is on garden- and vine-to-table and creating fine Virginia wine experiences. Quite possibly the most Instagrammed winery in the state, Pippin Hill offers a variety of ways to enjoy elevated food and wine, perfectly documenting it all the while. Tastings, estate tours, cooking and wine schools, and fine dining Vintners Table experiences featuring multi-course meals are all possibilities. For a more casual excursion, make a reservation to sip and dine in the tasting room overlooking the grounds with camera-ready Blue Ridge views in the distance.

Wisdom Oak Winery

Nestled on 126 acres, Wisdom Oak has multiple varietals planted including chardonnay, petit manseng, cabernet sauvignon, cabernet franc, and merlot. A small batch boutique winery, owners Jason and Laura Lavallee have crafted an “off the beaten path” experience, like those they have most enjoyed while visiting winemaking regions around the world.

Chestnut Oak Vineyard

Small, modern, and mighty is the perfect way to describe Chestnut Oak Vineyard. Producing small batches of red and white varietals, in a beautiful and vibrant setting, their goal is to provide a wonderful Virginia wine tasting. Bonus: seating areas provide an up-close-and-personal view of the grapevines, creating a truly immersive experience. Plan a weekend visit to enjoy a picnic with friends on their lovely grounds or add it to your Monticello Wine Trail itinerary.

Keswick Vineyards

Dedicated to creating superior wines, Keswick Vineyards invites you to enjoy a relaxing afternoon on the covered porch or bring a picnic to enjoy al fresco while sampling some of its exclusive tasting room selections. New to the Keswick experience is a mini golf course, complete with wine barrels throughout to hold your glass. Beer and cider offerings round out the experience—Keswick truly offers something for everyone.

Hark Vineyards
Hark Vineyards

Hark Vineyards

Sustainability, great views, and wine all in one place! As outdoor lovers, Aaron and Candice Hark were careful to cultivate the land with both gathering spaces and places of quietude in mind. They also installed a 103-kilowatt solar panel system atop the winery building’s roof, which will offset 3.7 million pounds of carbon dioxide over the next 25 years. Enjoy wine and a BYO picnic (fire pits are available during the winter) or purchase cheese, crackers, and even chocolate at the tasting room.

Barboursville Vineyards

Luca Paschina, Barboursville’s resident winemaker for more than 30 years, holds the most diverse and extensive record of honors among all his peers in Virginia. According to Luca, “the estate of wine is a divine gift without borders, linking humanity and our diverse cultural backgrounds to their most elemental and their most celebratory nourishment.” Considered one of the leading wineries in Virginia, and also one of the oldest, Barboursville wine was selected to be served to Queen Elizabeth II during her 2007 visit to Virginia. Discover the newest vintages in the tasting room, then purchase a glass and enjoy a historic stroll around the Barboursville Ruins; Thomas Jefferson’s mansion for Governor James Barbour which was mostly destroyed by a fire on Christmas Day 1884. 

Sip cellared vintages alongside culinary pairings in the Library 1821 as you overlook an expansive slope of cabernet franc vines and the Blue Ridge Mountains.

Moss Vineyards

Dramatic views and design alongside delectable wine—and cider—is what you’ll find at Moss Vineyards. Atop the mountain in Dyke, Virginia, Barry and Ellen Moss have created quite the getaway featuring small batch, estate grown wines and now a dry cider (the gold medal winner) for guest enjoyment. You’ll want to come prepared with outside food since you’ll be in no rush to leave this fairytale location.

With a bounty of wineries along the Monticello Wine Trail, it’s worthwhile to plot out your route and visit a few each day. Never fret, many of the wineries listed above offer on-site lodging with breathtaking landscapes ranging from lush open fields to the Blue Ridge Mountains. All you have to do is sit back, sip, and drink in the sunset before heading out to your next destination on the trail. Start planning your winter winery getaway today at!

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