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Discover the Monticello Wine Trail

Welcome to the Monticello Wine Trail — a vibrant tapestry of 40+ boutique wineries nestled in the foothills of the Blue Ridge Mountains, just minutes from downtown Charlottesville. Named “Wine Region of the Year” by Wine Enthusiast in 2023, this dynamic trail offers a memorable blend of history, terroir, and unforgettable sipping experiences.

Here, you’ll explore vineyards planted on granite-rich clay soils within the Monticello AVA — the same land where Thomas Jefferson first envisioned American winemaking. From elegant Cabernet Franc and Viognier to bold new blends, each tasting room invites discovery against scenic vistas, relaxing patios and a welcoming local vibe.

Whether you’re planning a day trip or a weekend getaway, the Monticello Wine Trail invites you to sip, explore and savour the essence of Virginia wine country.

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Monticello Wine Trail Wineries

Virginia AVAs Regions and Trails

Afton Mountain Vineyards

Some of the oldest vines in Virginia

Afton Mountain Vineyards is one of Virginia's first farm wineries with our oldest vines dating from the late 1970's. Our focus is on making wines of exceptional quality from our own estate-grown grapes. Our Tasting House is surrounded by vineyards, 360 degree mountain views and sits beside a 13 acre lake. We grow 11 varieties on 25 acres. "Grapes don't grow in ugly places"® Come see for yourself!

Barboursville Vineyards

Virginia's Most Honored Winery

Barboursville Vineyards in Virginia offers an unforgettable wine country experience, blending sustainable winemaking, rich history, and award-winning wines. Visitors enjoy scenic tours, intimate tastings, and fine dining at Palladio Restaurant. With iconic wines and historic Jefferson-designed ruins, Barboursville invites guests to immerse in Virginia’s finest wine culture and landscape.

Blenheim Vineyards

Single Vineyard, Small Parcel Wines

Blenheim Vineyards is a winery dedicated to making high quality wines that reflect the climate, soil and beauty of the landscape. Founded in 2000 on the historic Blenheim estate in Albemarle County, the goal at Blenheim Vineyards is to bottle wine from single vineyards and small parcels to capture the distinct characteristics of each site.

Designed by owner Dave Matthews and master craftsman William Johnson, the winery at Blenheim Vineyards provides a unique and intimate setting for tasting wine. Its great windows allow visitors to gaze out over vineyards to Jefferson's "sea view" beyond. Paneled glass floors provide a bird's-eye view of the wine production facilities below.

Brent Manor Vineyards

Old and New World Wines

Nestled in the hills of Virginia Wine Country in beautiful Nelson County just South of Charlottesville, The Brent Manor Vineyards welcomes you to a mix of the New World and the Old World.

Caihailian Vineyard

Caihailian Vineyard is owned by Bob and Anne Ramsey, and is named for their three fantastic kids: Cailin, Hailey, and Iain. Bob manages the 2.5 acre vineyard with an incredible amount of patience. Caihailian is located southwest of Charlottesville on the road to Wintergreen Resort, in the Monticello AVA.

Back in 2006 the Ramsey family harvested about 350 lbs. of grapes from the entire vineyard. Currently, they can get the same 350 lbs. from just one and a half rows. Fast forward to 2017, they harvested a whopping 6.8 tons (13,600 lbs.),

DelFosse Vineyards and Winery

Inspired by the French Masters

DelFosse Vineyards & Winery is located in central Virginia only a short drive south Charlottesville. Delfosse is inspired by the French Masters. Come taste our award-winning wines while you enjoy our scenic vistas, terraced vineyards, picnic areas, 6.2 mile hiking trail, streams and lake.

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