Inspired by Thomas Jefferson’s bold dream to create vineyards near his home in Virginia, the Monticello Wine Trail consists of over 30 wineries that produce some of the highest-quality grapes and wines in the world. Only an hour away from Richmond, Virginia, spend the day on the Monticello Wine Trail in Charlottesville, home to the celebrated wineries and vineyards of the Blue Ridge Mountains. On the Monticello Wine Trail, explore Virginia’s bucolic countryside. Sample the regional wine from some of the best Charlottesville wineries, meet the winemakers, and take in Virginia’s rich cultural history. With many vineyards and wineries to choose from, this shortlist includes historic vineyards, wineries and a cidery.
And while I’m not encouraging anyone to travel right now during the crisis, consider visiting this beautiful region when the experts say that it is safe to do so.
Monticello Wine Trail: Wineries in Charlottesville
An Easy Day Trip From Richmond, Virginia
Early Mountain Vineyards
Early Mountain Vineyards is an esteemed 55-acre vineyard in Madison, Virginia. This small town has only 221 residents and sits comfortably in the lush green pastures of the foothills of the Blue Ridge Mountains. Its picturesque scenery is nothing short of stunning, and it might even make you forget about visiting the other surrounding Monticello wineries and vineyards.
Early Mountain Vineyards offers award-winning wines that are known for historical consistency. They also serve a full menu of wine-friendly foods including artisanal cheese, fresh pasta, salads, and sandwiches. All of the food comes from local farms and dairies.
Early Mountain Vineyard Address: 6109 Wolftown-Hood Rd, Madison, VA 22727
“In 1774, Thomas Jefferson and Italian Filippo Mazzei established vineyards on land adjoining Monticello, the site of present-day Jefferson Vineyards, Virginia’s premiere small production winery.” – Jefferson Vineyards. Almost 250 years later, the tradition of Jefferson Vineyards lives on.
This charming vineyard offers more than just a presidential reputation and a fabled legacy. It also boasts savory wines and has one of the best pastoral views in Charlottesville, Virginia. This family owned winery feels like a scene out of a Faulkner novel. From any spot on the property, marvel at the beautiful foliage that’s unique to the Blue Ridge Mountains.
While relishing in the splendor of the vineyard, don’t forget to enjoy the vineyard’s award-winning Pinot Gris, Chardonnay, Riesling, Viognier, Merlot or Cabernet Franc. The Estate Reserve and Virginia’s first Petit Verdot are also excellent choices.
Jefferson Vineyards Address: 1353 Thomas Jefferson Pkwy, Charlottesville, VA 22902
Bold Rock Cidery
Founded in June of 2012, Bold Rock has become one of the nation’s largest independently-owned cider companies. Unlike the other locations on this list, Bold Rock specializes in hard cider, which is fermented apple juice. Since the apples are grown close by, they pick the apples at the peak of their freshness and extract 85 percent of the apple’s juice for the cider.
The Carter Mountain Orchard is just minutes outside of Charlottesville, Virginia. It has breathtaking scenic views, and you can enjoy the unique experience of picking your own fruit in the apple orchard. They also offer tastings, space for private events, and trendy merchandise. Since this is a seasonal location, check the website for the latest hours.
Carter Mountain Orchard Address: 1435 Carters Mountain Trail Charlottesville, VA 22902
Glass House Winery
Located in Free Union, Virginia, Glass House Winery is a 12-acre boutique artisanal winery that offers a one-of-a-kind tropical experience. Glass House Winery is the brainchild of owners Jeff and Michelle Sanders. It combines Michelle’s love for concocting unique and delicious chocolates with Jeff’s botanical prowess.
The Glass House Winery’s attached temperature-controlled glass conservatory provides a relaxing space to enjoy the tropical foliage, handmade chocolates and wines. There’s also a deck overlooking the lake and picnic tables.
While exploring the tropical ambiance and decor, pair some of Michelle’s mouth-watering chocolates like the Red Wine Cream Chocolate or the Salted Caramel Chocolate with Jeff’s award-winning 2015 Viognier or 2014 Cabernet Franc.
Glass House Winery Address: 5898 Free Union RoadFree Union, VA 22940
Pippin Hill Farm & Vineyards
Nestled in the middle of the picturesque Blue Ridge Mountains, Pippin Hill Farm & Vineyards offers the ultimate experience for those looking for farm to table food paired with award-winning wine. With almost 90 tons of grapes, including ten different varieties, grown on the property, Pippin Hill has its own signature Sauvignon Blancs, crisp Blanc de Blancs, Chardonnays, Cabernet Francs, and more. To spotlight local producers, Pippin Hill hosts Featured Farmer Fridays, a mini-farmers market that highlights the produce of local farmers. Visit Pippin Hill as a stop on the Monticello Wine Trail or book your own private event.
Pippin Hill Farm & Vineyard Address: 5022 Plank Road, North Garden, VA 22959
Producing wine since 1990, the Thatch Winery is uniquely named for the roof on the building where the wine is made. Thatch Winery is the only winery in the United States with a custom, hand-crafted, thatched roof made from imported Turkish water reed.
Located on 60 acres in Charlottesville, Virginia, visitors get to step back in time while experiencing the newly renovated tasting room and loft. As a maker of over a dozen wines, Thatch produces a wide variety, and each wine has a distinctive balance and complexity. Enjoy Thatch’s wines anywhere on the property including the gardens, patios, a terraced deck, two fireplaces, and three tasting bars.
Open daily for tastings and tasty bites, on a behind the scenes vineyard tour, taste six specially curated wines, learn about the winemaking process from vine to bottle, and check out the barrel room. Since reservations are required and there is a four-person minimum, book early and bring a few friends.
Thatch Winery Address: 1650 Harris Creek Road, Charlottesville, VA 22902
Just a few miles from James Monroe’s Highland, Trump Winery sits on a stunning 1,300 acre lot. It’s the largest vineyard in Virginia. Some folks say the Trump Winery is magical and hosts the most memorable events. Their wine has won numerous national and international medals. The best part is, you can spend the day enjoying the wine, and then sleep the night away at their boutique luxury hotel, Albemarle Estate at Trump Winery.
A stay at the Albemarle Estate is a must. Some have called it “one of America’s true treasures.” This 26,000 square foot, 45-room mansion, offers guests a night of elegance. There are ten luxurious guest rooms, each with detailed decor including twenty-foot hand-carved plaster ceilings, antique English rococo mantels, hand-painted wallpaper, crystal chandeliers, and more.
The Trump Winery offers gourmet cuisine and breathtaking views of the vineyard. If you try the wines at Trump Winery once, you might become a regular.
Where To Stay in Richmond
When planning a trip to Richmond, use Hotel Planner to help you find affordable and discounted hotels nearby. Create the perfect itinerary for your upcoming trip to the capital city and beyond with insightful tips and sample itineraries. Hotel Planner also shares average nightly rates by star rating. Hotels are even categorized by “luxury” and “affordable” groups. Each features notes about the property’s amenities including proximity to the airport and complimentary coffee. As you plan a trip to Richmond and neighboring Monticello Wine Trail, the birthplace of American wine, read the guest reviews to make sure that you’re picking the right accommodation for your travel style.
Danielle Desir is a financially savvy traveler, 5x author, and podcaster. She paid off $63,000 of student loan debt in 4 years, bought a house at 27, and has traveled to 27 countries. She refuses to let her financial responsibilities hold her back from living life on her terms. Listen to The Thought Card Podcast here.