Follow the Monticello Wine Trail: Your Guide to Charlottesville Wineries

Virginia is the birthplace of American wine, so it should be no surprise that the wines produced in the Monticello American Viticultural Area (AVA) rival established Old World vintages. Amid the backdrop of the Blue Ridge mountains, the region was named the Wine Enthusiast’s Wine Star Awards 2023 Wine Region of the Year, beating out international destinations in France and other noteworthy wine destinations. 

The Monticello Wine Trail has 40+ wineries within a 25-mile radius of Charlottesville to sip and savor, with much more to do and see. From nearby hiking trails and local businesses to beautiful bed and breakfasts and resorts, the Monticello region is full of beautiful experiences across Virginia’s wine country. Sip across the Commonwealth with dozens of wine trails and over 300 vineyards and wineries that pay homage to Virginia’s breathtaking beauty and wine history.

Find more ideas for what to do after your winery tours here. 

JEFFERSON’S WINE LEGACY

Beginning with the first colonists in America, Virginia has a rich history of wine and winemaking. The colonists faced many plights in their efforts of winemaking from the unfamiliar grapes and soil to weather and phylloxera challenges that threatened the crops. With robust perseverance, the early settlers continued to try their hand at grape growing, eventually leading to later success in Virginia’s vineyards. Claimed as the birthplace of American wine, Virginia has become a leader in the industry, ranked 6th for the most wineries per state.

And while it started with early colonists planting vines, wine became a focal point in Virginia when Thomas Jefferson became the President. Jefferson was heavily motivated by European influences on wine, taking inspiration from light wines from France and Italy as a way to break away from British effects on alcoholic beverages in the colonies. His love of wine stemmed from his experiences in France, beside French philosophers, and among the Bordeaux and Burgundy vineyards that held esteemed wine praise. 

Thomas Jefferson, alongside George Washington, George Mason, and 25 other influential leaders, created the Virginia Wine Company to establish vineyards as a cash crop in the Commonwealth. Jefferson soon began experimenting with viticulture by working alongside Italian viticulturist Filippo Mazzei at his home at Monticello. While his own crops didn’t show much success at the time, his determination to bring quality wine to the United States shone through and many winemakers took encouragement from the European influences that Jefferson emphasized.

The boundaries of the Monticello AVA were inspired by Jefferson and his Monticello home, overlooking the Blue Ridge mountains in the Charlottesville region. His dream of a thriving Virginia wine industry has become a reality, with dozens of vineyards and wineries throughout the rolling mountains and every other region in the state. 

THE MONTICELLO AVA

Due to Prohibition in the 1920s, the American wine industry stalled, putting vineyard and wine advancements within the country back several decades. It wasn’t until the 1970s that the industry began to thrive once again. During this time, the Monticello region arose as a leader, with the Jeffersonian Wine Grape Grower’s Society (JWGGS) established in the 1980s. 

In 1982, the JWGGS proposed for an American Viticultural Area (AVA) to be established surrounding the Charlottesville region and for it to be known as the Monticello AVA due to Jefferson’s historical influence on wine and the area. In 1984, the proposal was approved due to the AVA’s nationally recognizable name, its historical significance, and its unique geographical features. 

Unique to the Monticello AVA are the Blue Ridge Mountains that usher in cold air from the valleys and bring in warm air to the soil, making the climate conducive for grape growing. The mountains provide protection from winter winds and Virginia’s warm summers perfect the Vitis vinifera vines that were brought over from Europe and transformed into unique Virginia wines. The region boasts bright and flavorful New World wines that take on bold and fruit forward tastes, influenced both by European techniques and varietals and the American terroir and viniculture practices. Chardonnay, Cabernet Sauvignon, Cabernet Franc, and Viognier stand out in the Monticello AVA with unique Virginia flavors brought by award-winning winemakers and vineyards.

NOTABLE WINERIES NEAR CHARLOTTESVILLE

Jefferson Vineyards

Jefferson Vineyards operates on the very same estate where Thomas Jefferson tried his hand at winemaking with the assistance of Filippo Mazzei. The vineyards were reestablished in 1981 after Mazzei’s property, Colle, was dismantled in the 1900s and rebuilt to honor the history and winemaking traditions of the region.

Home to Virginia’s flagship varietal, Viognier, and many other award-winning wines, Jefferson Vineyards grows several varietals over their dozens of acres. They offer seasonal wine flights, wine glasses, and wine bottles in their tasting room to give guests a personalized experience for whichever wine they prefer. Summers at the vineyard are beautiful with lush green spaces and music in the garden for tasting delights.

King Family Vineyards

King Family began their story in 1996 after purchasing the 327-acre farm in Crozet. A few years later, when a man named Tom Vandenberg asked to lease some of the land for a vineyard, they started their journey into the wine industry. Since 2002, they’ve been operating the winery and producing top notch wines. King Family Vineyard’s Meritage, a blend of Cabernet Franc, Merlot, Petit Verdot, and locally-sourced Malbec, has won Silver, Gold, and Virginia’s Cup awards for its unique red blend that makes King Family Vineyards stand out. 

Open daily, the tasting room offers options for self-guided tastings or guided wine flights. Additionally, King Family is well-known for its polo matches, which are held every Sunday from Memorial Day weekend through mid-October. 

Barboursville Vineyards

The Barbour family preserved this estate from the 18th to the 20th centuries through agricultural innovations and attempts at bringing viticulture to the land. In the 1970s, heir to the property Gianni Zonin worked to plant vineyards at Barboursville and create the winemaking legacy that Thomas Jefferson dreamed about for the Charlottesville area. 

The entire estate is open to wine tastings, from the Discovery Room, where you’ll find the broadest range of tasting options, to Library 1821, with a changing selection of flights and seasonal offerings. Picnic on the grounds or take a strolling tour of Thomas Jefferson’s Landmark Ruins that were built for Virginia Governor James Barbour. Winning praise across the country and the world, Barboursville combines Italian influence with Virginia wines, especially with their landmark Octagon, a selective red blend that’s unique to the terroir. 

AWARD-WINNING WINEMAKERS

Michael Shaps

After living in France and studying wine in Burgundy, Michael Shaps moved to Virginia in 1995 to bring his wine expertise to the U.S. and work at Jefferson Vineyards. He later moved to partner with King Family Vineyards while making wine on his own, eventually opening Virginia Wineworks in 2007. His wines and work with wineries have received national accolades, with one of his partners winning the Virginia Governor’s Cup in 2017. Two of his tasting rooms are found in Charlottesville–Michael Shaps Winery and Wineworks Extended. Focused on small batch wines, Michael Shaps brings French inspiration into all of his wine production.

Luca Paschina

As a protege of Gianni Zonin at Barboursville Vineyards, Luca Paschina has been the resident winemaker at Barboursville since 1990. He created the flagship blend, Octagon, for the vineyard, leading them into much success and praise for the combination of traditional Italian and Virginian techniques in winemaking. Taking care to note the unique terroir of the Monticello AVA, Paschina has perfected his winemaking skills, bringing the well-deserved spotlight to shine on Virginia’s wine industry. 

Gabriele Rausse

Arriving in Virginia from Italy as a friend of Gianni Zonin, Gabriele Rausse began working with Virginia wine in 1976 at Barboursville Vineyards. In 1981, he moved towards partnering with Jefferson Vineyards, weaving in Virginia’s rich wine history at both entrepreneurial efforts. In the 1990s, he opened Gabriele Rausse Winery in the Monticello AVA and has created a reputation for himself as the “father of Virginia wines.” Taking inspiration from Jefferson’s history on winemaking as well as the steadfast European techniques, his innovations create unique blends of wine with bright and bold flavors that hold national prestige. From Chardonnay to Cabernet, he produces a wide variety of wines that stand up to the best vintages in the world. 

MONTICELLO WINE TOURS

Hop on Cville

Hop on Cville offers a variety of tours, from seasonal Tacky Lights and Wine Tours during the holidays to brewery, cidery, and winery group tours in the Charlottesville area throughout the year. Starting at $45 per person, you can choose your route and experience delicious food, wine, and beer from a variety of Virginia establishments.

Tipsy Wagen Tours

Looking for a unique wine tour experience? Tipsy Wagen has you covered. Hop into the vintage Volkswagen bus, charmingly named Mable, and take a drive along the Virginia countryside, meandering through three different wineries in the Monticello AVA. Tours are offered during the year whether you’re looking for a public, private, or customized winery adventure.

Monticello Wine Tour

Monticello Wine Tour and Coach Co. have several opportunities for private wine and beer tours lasting around five hours with 3-4 stops. In luxury vans and SUVs, each tour can fit anywhere from 6-14 people, making it a perfect option for a celebration with friends in Monticello’s wine country. Also offering wedding charters, airport transportation, and for-hire shuttle services, Monticello Wine Tour and Coach Co. brings style to your transportation needs in Charlottesville.

Check out this page for more wine tour options for the Monticello Wine Trail. 

WINERIES WITH EXCELLENT FOOD PAIRINGS

Pippin Hill Farm & Vineyards

To get the most out of your wine tasting experience, visit Pippin Hill Farm and Vineyards and try their garden-to-table food pairings with the wines. Begin your wine journey with a tour of the estate, leading into the tasting room where you’ll sample six Reserve and Library wines. Finish with a seat at a tasting room table and  order signature dishes from the menu to pair with your favorite wine. Pippin Hill Farm and Vineyard’s food and wine tasting celebrates Virginia’s culinary and wine heritage with their extensive selection of farm-to-table delights and esteemed wines.

Veritas Vineyards & Winery

Relax in the beauty of the Blue Ridge while exploring wine and food tastings at Veritas Vineyards. Reserve a spot at the tasting room to sip on some of Virginia’s delicious vintages paired with a food menu that focuses on farm-to-table delights from spreads to sandwiches to salads. Their outdoor seating options create the perfect spot to take in the picturesque beauty of Virginia’s landscape on a warm, sunny day. 

Hazy Mountain Vineyards

In Afton, Hazy Mountain is a family-owned winery and vineyard surrounded by the scenic mountain beauty of over 86 acres of vines. The most popular guest experiences are the guided wine tastings, led by a knowledgeable team member who will walk you through a selection of six pre-selected wines. The tasting room features a specialized menu with snacks, shareables, and sandwiches that are inspired by Virginia’s wine history. A curated selection of wines from both Virginia’s Shenandoah AVA and Monticello AVA showcase Hazy Mountain’s connections to the Commonwealth.

Merrie Mill Farm & Vineyard

Merrie Mill Farm and Vineyard was officially established in 2017 after the Pelly family renovated the historical main house that was built in 1857. Using their love of architecture, wine, interior design, and the outdoors, the Pellys created this one-of-a-kind vineyard and winery. Working with their sister brand, Feast, Merrie Mill Farm and Vineyard serves farm-fresh food made with locally-sourced ingredients. Additionally, they offer Cake Bloom cakes from Charlottesville and Nightingale ice cream from Richmond, prioritizing local partners to create fantastic wine pairings. 

VINEYARDS WITH ON-SITE LODGING

After spending your day at one of the fantastic Monticello AVA wineries, stay in Charlottesville or the surrounding region to rest and relax while experiencing Virginia’s local delights.

The Farmhouse at Veritas Vineyards

The Farmhouse at Veritas Bed & Breakfast offers six elegant bedrooms on the property complete with an on-site restaurant serving delicious meals and a four-course wine paired dinner. Book here.

Afton Mountain Vineyards

Stay at the tranquil setting of Afton Mountain Vineyards in one of their guest cottages overlooking wildflower meadows and scenic vineyards. Book here. 

Barboursville Vineyards

With multiple options for lodging from the 1804 Inn to a number of cottages on-site, Barboursville Vineyards blends the site’s rich history with classic architecture and modern inspiration. Take a stroll right outside your door through the tranquil vineyard setting. Book here.

Hardware Hills Vineyards

Enjoy a front porch view of the vineyards at Hardware Hills’ guest cottage. Quaint and cozy, the cottage is a serene retreat right on the vineyard grounds. Book here. 

Pippin Hill Farm & Vineyards

The restored historic Crossroads Inn is located on the grounds of Pippin Hill Farm & Vineyards. Cooking classes, horticulture workshops, estate tours and tastings create a unique experience in Virginia’s wine country. Book here. 

PLACES TO STAY NEARBY

Boar’s Head Resort

For outdoor adventurers, wine enthusiasts, and leisure lovers alike, Boar’s Head Resort is a countryside retreat in the mountains of Charlottesville. Close to numerous wineries and vineyards, Boar’s Head Resort offers guests a luxury stay in wine country. Book here. 

The Clifton

A boutique hotel in Virginia’s rolling countryside, the Clifton is only a short drive away from Charlottesville’s downtown scene and surrounding wineries. Book here. 

The Draftsman

For a stay within the city limits, visit The Draftsman Hotel in downtown Charlottesville, where you’ll be close to Charlottesville’s Downtown Mall and the University of Virginia campus while just a short drive away from fantastic wineries and vineyards. Book here. 

More lodging options: 

Where to Stay (& Sip!) in Virginia Wine Country

Whether you visit during the gorgeous reds and oranges of the mountains in the fall, the frost-covered ground in the winter, the blooms of Virginia’s dogwood trees in the spring, or the rainbow of wildflower meadows in the summer, Virginia’s Monticello AVA has a unique scenic beauty that is sure to inspire any visitor. Sip your way through the mountains and stay in the Charlottesville region, taking in history, outdoor adventures, and more.

Looking for more wine inspiration in Virginia? Check out these articles:

• Wineries that Offer Stunning Views of Virginia’s Scenic Beauty
• Beyond the Wine: 11 Unique Virginia Vineyard Experiences
• The Greenest Vineyards: Virginia’s Eco-Friendly & Organic Wineries