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The Best Charlottesville Wineries on the Monticello Wine Trail

The Best Charlottesville Wineries on the Monticello Wine Trail

Did you know that Virginia is the birthplace of American wine? Yes, not California… Virginia! With that said, Virginia has over 300 wineries. So with all of the wineries to explore in such little time, we recommend going to the heart of Virginia’s wine country on the Monticello Wine Trail.

Why? Because the best wineries in Charlottesville, if not, the entire state of Virginia, can be found on the Monticello Wine Trail. There are 33 wineries on the Monticello Wine Trail that all span near the Blue Ridge Mountains.

The Blue Ridge Mountains and Charlottesville are two of the best places to visit in Virginia. So with a great glass of wine and the vibrant Blue Ridge Mountains, you can guarantee you will be surrounded by great beauty.

Thus, making the Charlottesville wineries on the Monticello Wine Trail, a great destination on an East Coast road trip. You can even turn your trip to a romantic getaway and stay at a winery bed and breakfast.

Here are five of the best Charlottesville wineries that should include in your weekend itinerary.

Full disclaimer –  We received complimentary wine tastings, dining, and accommodation during our trip to Monticello Wine Trail. As always, our opinions are non-biased and our own. We want to thank the wineries we worked with for their generosity. In addition, we want to thank everyone for following and supporting us on all of Our Sweet Adventures. 

Veritas Winery and Vineyard

Veritas Winery and Vineyard was our absolute favorite winery for several reasons. They have our favorite type of wine in the entire world, ice wine. In addition, they also have spectacular views of the Blue Ridge Mountains, offer wine tours and they have the most lovely bed and breakfast you can imagine.

We highly recommend this to be your last winery stop during your 2-day Monticello Wine Trail because staying at the Farmhouse at Veritas is an incredible experience. You can enjoy complimentary wines, champagne, a farm to table dinner, cozy accommodations and a delicious breakfast to continue your wine journey.

In addition to the bed and breakfast, a visit to Veritas Winery and Vineyard is an incredible winery that should not be missed on the Monticello Wine Trail. It is truly one of the best Charlottesville Wineries, if not the world. We have never liked so many wines from the same winery before and we’ve been to plenty. During your visit to the winery be sure to enjoy their wine tasting. You will instantly fall in love with Veritas wide selection of beautiful wines as we did.

Furthermore, you should also enjoy their wine tour where you can learn about the history of the owners and property itself. If you are interested in the wine tour, be sure to call ahead and make reservations for it. Lastly, enjoy their patio that looks out to the vineyards with the Blue Ridge Mountains in the backdrop with a glass of wine and scrumptious appetizers. Their onsite restaurant, The Terrace, serves delectable sandwiches, salads, cheese, hummus and charcuterie.

Known For: Incredible views, delicious food, Starry Nights summer music series event and their B&B, the Farmhouse at Veritas.

Our Favorite Wines: Kenmar, White Star, Red Star, Club Cluvée and Rose 2017.

Tasting Price: Between 8-10 wine tastings for $10 per person. Group tastings of at least 8 people are $15 per person and reservations are required.

151 Veritas Lane
Afton, VA 22920
(540) 456-8000
Mon – Fri: 9:30am – 5:30pm
Sat – Sun: 11am – 5pm

Jefferson Vineyard

A visit to the Monticello Wine Trail cannot be complete without a visit to Jefferson Vineyard. The name of the estate says it all. The vineyard is rich with history from Thomas Jefferson and his close Italian friend and winemaker, Philip Mazzei. Together they helped create Virginia as the birthplace of American wine. Mazzei did everything he could to help bring Jefferson’s dream of American wine into a reality. Sadly it never went into fruition due to the vines being destroyed. However, Jefferson would be proud to see this land and vineyard has honored him admirably by producing fine wines.

The Jefferson Vineyard has been in the Woodward family for three generations. So guests can expect great care, passion and love brought into each bottle of wine. We certainly tasted these characteristics as the Jefferson Vineyard was one of our favorite wineries on the Monticello Wine Trail. What makes Jefferson Vineyard one of the best wineries in Charlottesville (besides taste), is their labels. As cat lovers, we are a little biased with one of them, since it has a cat on the label. The cat is made in memory to the owner’s cat, Sam. Furthermore, the more unique wine labels are a simple, naked bottle with Thomas Jefferson’s handwriting. It is by far the coolest wine bottle and very fitting being in the birthplace of America’s wine.

Jefferson Vineyard is one of the best Charlottesville wineries on the Monticello Wine Trail

Visitors can enjoy three different wine tastings at Jefferson Vineyard – classic, private and library. The classic tasting offers eight wonderful wines. The library wine tasting is offered during select times of the year and provides their most premium award-winning library wines. The private tasting says it all, but also includes the eight classic wines in addition to two premium library wines.

Known For: Rich history, incredible views and Virginia’s first Petit Verdot

Our Favorite Wines: Vin Blanc 2017, Chardonnay Reserve 2017 and Petit Verdot 2016

Tasting Price: Classic tasting of 8 wines for $12 per person. For a private tasting, it must be booked in advanced and includes 10 wines (8 classic and 2 library) for $25 per person. Contact estate about the premium library tasting. Group tastings of at least 8 people are asked to contact the estate for arrangements. Guests get to take home a signature wine glass.

1353 Thomas Jefferson Parkway
Charlottesville, VA 22902
(434) 977-3042
Open daily: 11am – 6:15pm

Early Mountain

Early Mountain is one of the best wineries in Charlottesville for tastings, great atmosphere, special event space and of course, their wine. Though there are several aspects that make Early Mountain stand out on the Monticello Wine Trail, it is their dedication to showcasing the best wine in Virginia. Early Mountain is committed to not only producing high-quality wine but to also promote Virginia as a world-class wine region. With that said, visitors can find a “Best of Virginia” wine selection in Early Mountain’s tasting room.

Enjoying Early Mountain Vineyard on the Monticello Wine Trail

Furthermore, their dedication to supporting Virginia does not end with the wine. Early Mountain also features a full menu using produce from local farms, dairies and ranches. So when visitors come for the award-winning wine, they can pair it with delicious cuisine. Our three favorite must order items are the pimento cheese, Cubano and chicken salad sandwich. They were absolutely divine!

There is so much to enjoy during your visit to Early Mountain. Guest’s can enjoy the beautiful tasting room, or sit on the lovely patio soaking up the mountainous scenery. They can also ask about a wine tour and see the process of how Early Mountain produces their fabulous wines. Better yet, book a special event in their gorgeous event spaces. We were ready to renew our vows when we saw all of their private special event rooms. From a private cellar dining room to a grand ballroom – we were sold!

Known For: Number one Tasting Room in America, “Best of Virginia” wine selection, patio with scenic views, delicious cuisine, year round events (concerts, festivals, dinners, classes) and special event space.

Our Favorite Wines“Young Wine” Vidal 2017, Stone Mountain Chardonnay 2016 and Eluvium 2014

Tasting Price: Their wine tasting includes 6 of the current releases for $12 per person. The “Cheers tasting includes 6 of the current releases in addition to three of their precious wines for $18 per person. Group tastings of at least 15 people are asked to make reservations in a special event room. Guests get to take home a signature wine glass.

6109 Wolftown-Hood Road
Madison, VA 22727
(540) 948-9005
Wed – Mon: 11am – 6pm
Closed on Tuesdays

Barboursville Vineyards

Barboursville Vineyards is one of the most popular wineries on the Monticello Wine Trail because of its superb wines and rich history. The vineyard occupies the estate of James Barbour, Virginia’s Governor during the War of 1812. Furthermore, the vineyard’s estate also has the ruins of Governor Barbour’s mansion which was designed by Thomas Jefferson.

There is no better winery to get a grand wine tasting experience, than at Barboursville Vineyards. Guests who choose the classic tasting get to partake in almost 20 wine tastings! Starting with exquisite whites, to vibrant reds and finishing on a sweet note with dessert wines. Another amazing wine tasting experience is their Library 1821 which features a (always changing) selection of 20 flights of older vintages paired with bite-sized culinary fare.

The most popular and famous award-winning wine at Barboursville Vineyards is their Octagon wine. It is comprised of a beautiful blend of Merlot, Petit Verdot, Cabernet Franc, and Cabernet Sauvignon. For an additional price in the classic tasting, guests can enjoy an ounce of the Octagon. Or you can enjoy it during the Library 1821 tasting. We highly recommend it, as the Octagon is as brilliant as everyone says.

Barbousville Vineyard is not only one of the best Charlottesville wineries, but also has one of the best wines in the country.

Barboursville Vineyard also has Palladio Restaurant which serves lunch and dinner to guests. As well as a 1804 Inn for guests to stay and enjoy the full Barbousville experience. It is truly an amazing place to escape and relax in Virginia’s wine country.

Known For: Octagon wine, rich history and expansive wine tastings.

Our Favorite Wines: Pinot Grigio 2017, Barbera Reserve 2016, Octagon and Phileo.

Tasting Price: Their wine tasting includes at least 17 of their current vintages for $7 per person. The Library 1821 tasting of older vintages paired with bite-sized culinary fare for $25 per person. Guests get to take home a signature wine glass.

17655 Winery Road
Barboursville, Va 22923
(540) 832-3824

Mon – Sat: 10am – 5pm
Sun: 11am – 5pm

Pippin Hill Farm

Pippin Hill Farm is exactly the experience we were wanting during our Monticello Wine Trail – good wine, delicious food, charming ambiance, and great views. What sets Pippin Hill Farm apart as one of the best wineries in Charlottesville, is their farm to table dining experience with the best views on the Monticello Wine Trail. We fell head over hills with Pippin Hill Farm the moment we drove through their vineyard. The entrance welcomes you with grapes hanging on the vineyards left and right as you drive through. Then you are greeted with a flowering hedge that takes you to stunning views of rolling mountains.

Stunning views at Pippin Hill Farm along the Monticello Wine Trail

We instantly wanted to renew our vows (yes, again) at Pippin Hill Farm. So with that said, it is one of the most beautiful properties with a variety of special event space. One space that completely stole our hearts is their patio dining area. It is the perfect place to enjoy lunch and wine with your friends or loved ones.

Pippin Hill Farm is a family owned winery & vineyard that is committed to sustainable viticulture, farm to table dining experiences and supporting local farmers and producers. With that said, they have their own Chef’s Garden. Their menu at their Tasting Room includes a guide of what they grow and when they harvest each vegetable, fruit and herbs. Then the menu also informs you which entrees include produce from their Chef’s Garden. To continue the farm to table experience, guests can also take a stroll through the garden. The culinary journey does not end there, they also have their own free range chicken coop! So when you are looking to order an appetizer, I highly recommend the Deviled Eggs. They were heavenly!

Known For: Farm to table dining experiences, cooking classes, incredible views, and a charming country ambiance.

Our Favorite Wines: Zero White 2017, Viognier 2017 and Merlot Reserve 2015.

Tasting Price: Their Classic Tasting includes five wines for $10 per person. The Reserve Tasting includes four of their vintage wines for $13 per person. Guests can take home a signature wine glass for $1.

5022 Plank Road
North Garden, VA 22959
(434) 202-8063
Tues – Sun: 11am – 5pm
Closed on Mondays

I hope I have inspired you to take a trip to the heart of Virginia’s wine country. As you can see, these are truly some of the best wineries with unique and amazing experiences along the Monticello Wine Trail! It is without a doubt, the perfect getaway to savor fantastic wines and delicious farm to table dining experiences.

Michelle Dodson

Monday 5th of September 2022

Can't wait to visit next week!


Monday 5th of September 2022

I hope you enjoy!!!! All the wineries are lovely with some amazing views :)

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