Cunningham Creek Winery & Brewery is a family owned & operated small lot winery and brewery. We specialize in small lot finely crafted French varietals and Bordeaux blend wines and craft beers on tap. We're located on the Monticello Wine…
Best of the Best
Charlottesville was named Wine Region of the Year by Wine Enthusiast, and now you can find the best of the best by tasting the gold medal winners of the Virginia Governor's Cup. The Virginia Governor’s Cup is the premiere wine competition within Virginia, with over 620 of the best Virginia wines, ciders, and meads submitted and sampled by world-class judges. The rating system is based on a 100-point scale, also used by Wine Spectator, Wine Advocate, Wine Enthusiast, and Wine & Spirits.
The judging is rigorous. All wines go through a preliminary round of blind tasting. Qualifying wines then move on to the final round where each is reviewed by twelve judges. A wine’s average score is used to determine its medal status. Judges comment on a wine’s appearance, aroma, flavor, overall quality, and commercial suitability.
The twelve top-scoring wines are honored with inclusion in the prestigious Governor’s Case. These wines represent the very best of the best Virginia wines. While we wait on the 2025 results to be announced, it's worth mentioning that half of the wines in the 2024 Governor's Case came from the Monticello Wine Trail!
King Family Vineyards, 2019 Meritage
Afton Mountain Vineyards, 2019 T
Barboursville Vineyards, 2019 Paxxito
Hark Vineyards, 2019 Spark
Michael Shaps Wineworks, 2020 L.Scott
Mountain and Vine Vineyards and Winery, 2022 Chardonnay
The top wine is the recipient of the Governor's Cup. In 2024, King Family Vineyards, received this top honor!
-
Get Directions (434) 207-3907
-
Get Directions (434) 264-6727
Escape to Eastwood, a food and wine destination on the Monticello Wine Trail.Located in the heart of Virginia’s Wine Country, and only five miles from downtown Charlottesville, Eastwood Farm & Winery offers award-winning wines, along with beers and ciders, in…
-
Get Directions (434) 977-3042
Thomas Jefferson had a deep interest in wine and was known for his efforts to promote viticulture in Virginia and the United States. To that end, he convinced Italian vintner Philip Mazzei to settle in Albemarle County in late 177…
-
Get Directions (434) 266-9909
Situated on 1,300 acres of breathtaking scenery, Trump Winery is Virginia's largest vineyard and is located along the Monticello Wine Trail. Just minutes from downtown Charlottesville and historic sites Monticello and Highland, Trump Winery is producing sparkling, white and red…
-
Get Directions (540) 456-8667
Afton Mountain Vineyards is one of Virginia’s first farm wineries with original vines planted in the 1970s. Our focus is on making wines of unrivaled quality from our own estate-grown grapes. Surrounded by 360 degree mountain views, our Tasting House…
-
Get Directions (434) 252-2947
A historic Jeffersonian estate nestled in the Virginia countryside, Chiswell Farm & Winery invites guests to delight in locally-crafted vintages, panoramic views, and warm hospitality. Owned and operated by the Chiles Family, Chiswell continues a long legacy of Virginia agriculture…
-
Get Directions (434) 823-1486
Grace Estate Winery is located near Crozet and White Hall, Virginia, just 14 miles west of Charlottesville. All Grace Estate wines are made from grapes grown onsite at beautiful Mount Juliet Farm. At Grace Estate, we provide a unique hospitality…
-
Get Directions (434) 823-7800
King Family Vineyards is a family owned and operated vineyard and boutique winery located in Crozet, Virginia, 15 minutes west of Charlottesville, at the foot of the Blue Ridge Mountains. We are conveniently located to Rt. 250, the Blue Ridge…
-
Get Directions (540) 456-8844
Pollak Vineyards, a dream of Margo and David Pollak, is a boutique-sized winery on a 98-acre farm in Greenwood, Virginia, just west of Charlottesville. With the goal of making French-style wines from estate-grown grapes, the Pollaks have created a winery…
-
Get Directions (434) 823-7300
Stinson Vineyards is a family and winemaker-owned estate winery in Virginia’s Blue Ridge Mountains specializing in small lot wines with a distinct French influence. The father-daughter team of Scott Stinson and Rachel Stinson Vrooman was joined by Rachel’s husband Nathan…
-
Get Directions (540) 456-6350
Since our founding in 2016, Valley Road Vineyards’ goal has been to provide outstanding estate wines in a charming farm winery setting. Located in Virginia’s historic Monticello Viticulture Area (AVA), we have 12 acres under vine, with 7 more planted…
-
Get Directions (540) 456-8000
Veritas is a family-owned and run farm winery nestled in the foothills of the Blue Ridge Mountains. Andrew, Patricia, Emily, George, and Chloe Hodson share the common goal of making wines of the highest quality from the rich Virginia terroir…
-
Get Directions (434) 297-2326
Albemarle CiderWorks is a family-run Cidery and Tasting Room that produces cider from heritage varieties of apples that can thrive in Albemarle County,Virginia. Thomas Jefferson experimented with 18 or more varieties of apples at Monticello, only a few miles from…
-
Get Directions (434) 984-0774
CERTIFIED-ORGANIC AND YUMMY WINES!Virginia's only certified-organic vineyard and winery, Loving Cup is pioneering the future of East Coast grape-growing. Friendly, knowledgeable servers will direct through a full list of wines: dry or sweet, sparkling or still, red or white. Wines…
-
Get Directions (434) 296-3438
Known for his innovation and winemaking expertise, Michael Shaps has established himself at the forefront of the modern Virginia wine industry. He produces wines under the Michael Shaps label and for several prestigious wineries throughout the state.Founded in 2007, Michael…
-
Get Directions (434) 263-6100
Founded as Delfosse Vineyards and Winery, Mountain & Vine focuses on making estate grown, award winning wines.The location is exquisite, hugged between the hills, but with the elevation to guarantee not only flavorful wine but also breathtaking views. A brief…
-
Get Directions (540) 832-3824
Established in 1976 by Gianni Zonin, whose family has been producing wines throughout Italy since 1821, Barboursville Vineyards is dedicated to growing estate-bottled wines of European heritage which merit comparison with the finest wines of their kind, grown anywhere in…
-
Get Directions (434) 981-3793
Located in the heart of Virginia, the vineyards of The Barn at 678 represent the agricultural and adventurous spirits of co-founders Ricky and Lorrie Bryant. Turning their decades of experience in cultivation and land management to viticulture, they are excited…
-
Get Directions (540) 832-7440
Pioneers in Virginia wine since 1989. Horton Vineyards is home to the original Virginia Viognier and continues to explore with new varietals and techniques to achieve the very best that Virginia viticulture can produce.The tasting experience at Horton Vineyards is…
-
Get Directions (434) 244-3341
Keswick Vineyards is a family owned and operated winery and vineyard situated on the historic Edgewood Estate in Keswick, VA, about 15 minutes east of Charlottesville along historic route 231. Tastings are available daily from 10-5 (excluding major holidays) in…
-
Get Directions (540) 832-3895
Reynard Florence Vineyard is a small family owned and operated winery featuring hand crafted, award winning wines with vinifera varietals. Focus is placed on European – style wines that emphasize the subtlety and complexity of each vintage of our vineyard…
-
Get Directions (434) 212-3244
Start your Virginia wine adventure at the Southwest Mountains Vineyards!Southwest Mountains Vineyards is set along the Virginia foothills of the Southwest Mountain Range in Keswick, Virginia. Known for its idyllic scenery and pastoral vibe, Keswick is a beautiful and integral…
-
Get Directions (540) 219-1874
Woodbrook Farm Vineyard is a family owned and operated vineyard located near historic James Madison’s Montpelier. What once was a thriving thoroughbred racehorse training facility is now home to Woodbrook Farm Vineyard’s Training Barn Tasting Room. Our vineyard was planted…
-
Get Directions (434) 964-9463
Hark Vineyards is a family-owned winery focused on the belief that beautiful views and delicious wine can bring people together. Our grapes love it here. We think you will, too.
-
Get Directions (757) 647-9398
One of the newest tasting rooms in the Monticello AVA, Fallen Tree Vineyard is located in the stunning Crozet - White Hall region of western Albemarle County. Our vineyard enjoys 180 degree valley and mountain views.Varietals being produced include Chardonnay…
Gold medals were awarded to 155 wines from 87 Virginia wineries, cideries and meaderies after a series of rigorous blind tastings. Across the Monticello Wine Trail region, 25 producers earned 57 gold medals. Want to try these award-winning wines? We’ve divided the region into “neighborhoods” to help you organize your time and travels.
For each winery, we’ve added a brief overview to pique your interest – however, this just scratches the surface of what each one offers! Visit their individual websites to learn more.
Here are some tips for getting around and making the most of your travels:
- The Virginia Governor’s Cup has a passport app that tracks visits to wineries and earn rewards.
- Cville Hop-On Tours, Crozet Trolley, and Monticello Wine Tour & Coach Co. provide excellent tours to area wineries. Look to our wine tours page for upscale transportation options. Local companies can help you develop a personalized itinerary, so all you have to do is just sit back and enjoy the ride!
- Looking for a unique experience? Indian Summer Guide Service leads horseback rides through local vineyards. You could also work with Shaniece Be to organize a luxurious picnic - perfect for intimate gatherings, solo 'me time,' and more!
- Consider staying overnight at a vineyard! Visit the winery lodging page for a list of wineries with lodging and visit the Places to Stay page for a complete list of local accommodations.