Monticello Wine Trail

No single road: member wineries sit within about 25 miles of Charlottesville across Albemarle, Nelson, Orange, Greene and Fluvanna counties. Clusters include Route 151 near Afton, Crozet, Barboursville and the area south of Charlottesville.

Checked October 1, 2026 on the trail’s and each winery’s own website. Official trail site

• 44wineries listed
• 17towns
• 24serve food
• 36dog-friendly

The wineries (44)

14 of 44 wineries publish a tasting price. Sorted by town.

• Afton Mountain Vineyards

  Afton

  One of Virginia's early farm wineries, with first vines planted in the 1970s; makes Chardonnay, Cabernet Franc, Gewurztraminer and a traditional-method sparkling wine.

  • dog-friendly
  • picnic
  • live music
  • food

• Cardinal Point Vineyard & Winery

  Afton

  Family winery below Afton Mountain whose grower also makes the wines; list includes a vinho-verde-style white called Green and a hopped Chardonnay.

  • $25 for a guided tasting of 5 wines (weekends)
  • dog-friendly
  • live music
  • food
  • event venue

• Flying Fox Vineyard

  Afton

  Family-run winery making a core range of 8 Virginia wines since 2006, plus an experimental Sly Fox line and a vermouth.

  • dog-friendly
  • picnic

• Hazy Mountain Vineyards

  Afton

  Estate vineyard first planted in 2019, about 35 acres on south-facing slopes; also runs a brewery.

  • Guided tasting $20 per guest
  • brewery/cidery
  • food

• Valley Road Vineyards

  Afton

  Estate winery on Route 151; its 2023 Cabernet Franc Reserve won the 2026 Virginia Governor's Cup.

  • dog-friendly
  • picnic
  • live music
  • event venue

• Veritas Vineyard & Winery

  Afton

  Family-owned winery for about 25 years; winemaker Emily Pelton makes sparkling, white and Bordeaux-style red wines.

  • food
  • lodging
  • dog-friendly
  • picnic
  • live music

• Barboursville Vineyards

  Barboursville

  Founded in 1976 by the Zonin wine family of Italy; known for its Octagon Bordeaux-style blend, Cabernet Franc and Nebbiolo, on an estate with ruins of a Jefferson-designed mansion.

  • $20 per person
  • food
  • lodging
  • dog-friendly
  • event venue

• Burnley Vineyards

  Barboursville

  One of the oldest vineyards in the Monticello AVA, run by the Reeder family.

  • $8 per person for 12 wines

• Chestnut Oak Vineyard

  Barboursville

  Small-batch wines about 20 minutes from Charlottesville, served by the flight, glass or bottle.

  • Flights $15-$20
  • dog-friendly
  • picnic

• Reynard Florence Vineyard

  Barboursville

  Family-run small-batch winery in Orange County owned by Roe and Dee Allison.

  • Tasting flights $5-$15
  • live music
  • picnic
  • dog-friendly

• The Barn at 678 Vineyard

  Barboursville

  Winery founded by Ricky and Lorrie Bryant, pouring Chardonnay, Viognier, red blends and sparkling wines.

  • dog-friendly
  • food

• Blenheim Vineyards

  Charlottesville

  Founded in 2000 by Dave Matthews on the historic Blenheim Farm; about 30 acres planted across three vineyard sites.

  • $25 for a guided tasting of 5 wines
  • dog-friendly
  • picnic
  • food

• Eastwood Farm & Winery

  Charlottesville

  Women-owned, multi-generational winery making wines, ciders and beers; a second tasting room, the Virginia Wine Collective, is at 1585 Avon Street Ext.

  • food
  • live music
  • lodging
  • dog-friendly
  • brewery/cidery

• Gabriele Rausse Winery

  Charlottesville

  Small-production wines from Gabriele Rausse, sold under his own name and the Vino dal Bosco label.

• Jefferson Vineyards

  Charlottesville

  On the site Jefferson and Philip Mazzei chose for Virginia's first wine company; a commercial vineyard again since 1981.

  • live music
  • picnic
  • dog-friendly
  • food

• Knight's Gambit Vineyard

  Charlottesville

  Family-run, solar-powered winery with six estate wines from vines planted in 2003.

  • Flight of all six estate wines (price not listed)
  • dog-friendly
  • live music
  • event venue

• Michael Shaps Wineworks

  Charlottesville

  Founded in 2007; makes old-world-style wines under the Michael Shaps label and for other Virginia wineries.

  • picnic

• Mount Ida Farm & Vineyard

  Charlottesville

  Tasting room and taphouse opened in 2018 at Mount Ida Reserve, with just over 20 acres of vines and farm-brewed beer.

  • food
  • brewery/cidery
  • lodging
  • dog-friendly
  • event venue

• Oakencroft Farm & Winery

  Charlottesville

  One of Albemarle's first commercial vineyards (1980s), reopened under new owners; focuses on hybrid grapes and regenerative farming.

  • food
  • dog-friendly
  • event venue

• Roslyn Farm & Vineyard

  Charlottesville

  Farm estate first built in 1938 and renamed Roslyn Farm & Vineyard after a 2015 purchase; also a wedding and event venue.

  • event venue

• Trump Winery

  Charlottesville

  Large estate with 227 acres of vines, known for traditional-method sparkling wines.

  • $25-$45 per self-guided flight
  • food
  • lodging
  • dog-friendly
  • event venue

• Fallen Tree Vineyard

  Crozet

  Mostly dry-style wines made by Matthieu Finot, with valley and mountain views.

  • food
  • dog-friendly

• Grace Estate Winery

  Crozet

  All wines are made from grapes grown at Mount Juliet Farm in Crozet.

  • picnic
  • dog-friendly
  • event venue

• King Family Vineyards

  Crozet

  Family-owned winery with Matthieu Finot as winemaker; hosts polo on Sundays from Memorial Day to mid-October.

  • Guided tastings from $25
  • picnic
  • dog-friendly
  • food

• Stinson Vineyards

  Crozet

  Family and winemaker-owned estate making small-lot wines with a French influence.

  • dog-friendly
  • live music

• Chisholm Vineyards

  Earlysville

  100% estate-grown wines from a 12-acre vineyard at Adventure Farm, run by the Chisholm family since 1950; wines are made at Early Mountain Vineyards.

  • dog-friendly
  • picnic
  • live music
  • food
  • event venue

• Hark Vineyards

  Earlysville

  100% estate wines made on site by Jake Busching; its 2023 Cabernet Franc won the 2026 Monticello Cup.

  • $15 white tasting or $20 red/mixed tasting (4 wines, 2oz pours)
  • picnic
  • dog-friendly
  • food

• Mountain & Vine Vineyards and Winery

  Faber

  Terraced vineyard making French-inspired wines near Wintergreen.

  • lodging
  • dog-friendly
  • picnic
  • event venue

• Glass House Winery

  Free Union

  Winery with a tropical plant conservatory tasting room; also makes chocolates and beer.

  • lodging
  • dog-friendly
  • picnic
  • live music
  • brewery/cidery

• Horton Vineyards

  Gordonsville

  Three-generation winery in Orange County, open since 1989, pouring over 40 wines including fruit and dessert wines; an early grower of Viognier.

• Chiswell Farm & Winery

  Greenwood

  Owned by the Chiles family of Carter Mountain Orchard, grape growers for 30+ years; wines made by Michael Shaps and Matthieu Finot. Adults 21+ only, no dogs.

  • Build-your-own flight of 4 wines (price not listed); Reserve Tasting $30 per person by reservation
  • food

• Pollak Vineyards

  Greenwood

  Founded in 2003 on Mountain Hollow Farm; 34 acres of French vinifera grapes, all estate grown.

  • live music
  • picnic
  • dog-friendly

• Septenary Winery

  Greenwood

  Winery at historic Seven Oaks Farm using mainly old-world methods with fruit from two vineyards. Adults 21+ only.

  • picnic
  • dog-friendly

• Keswick Vineyards

  Keswick

  Family-owned winery making small lots, including Verdejo, Viognier, Norton and Touriga.

  • food
  • picnic
  • dog-friendly
  • live music
  • kids area

• Merrie Mill Farm & Vineyard

  Keswick

  Estate wines poured in a 5,000 sq ft tasting room built on the site of an old tractor barn.

  • Full-catalog tasting $60 per person with cheese and charcuterie
  • food
  • live music
  • dog-friendly
  • event venue

• Southwest Mountains Vineyards

  Keswick

  Estate winery in Keswick whose tasting barn is a restored 1903 structure.

  • food
  • dog-friendly

• Lovingston Winery

  Lovingston

  100% estate-grown wines since 2003 from 11 acres and eight grape varieties, including Pinotage.

  • lodging
  • dog-friendly
  • picnic
  • food
  • event venue

• Loving Cup Vineyard & Winery

  North Garden

  Certified-organic estate vineyard and winery.

  • dog-friendly
  • picnic

• Pippin Hill Farm & Vineyards

  North Garden

  Vineyard with a farm-to-table kitchen and event venue on Bundoran Farm; wines made by Michael Shaps.

  • food
  • lodging
  • dog-friendly
  • event venue

• Moss Vineyards

  Nortonsville

  Vineyard at about 1,000 ft growing Cabernet Sauvignon, Merlot, Petit Verdot, Viognier and Vermentino; also makes a hard cider.

  • $17 per tasting; $20 for groups of 7 or more
  • dog-friendly

• Woodbrook Farm Vineyard

  Orange

  Family vineyard on a former racehorse training farm near Montpelier; wines made with Michael Shaps Wineworks.

  • dog-friendly
  • picnic
  • live music

• Cunningham Creek Winery

  Palmyra

  Family boutique winery on a former cattle and hay farm, planted from 2012, about 12 miles from Jefferson's original vineyard.

  • dog-friendly
  • picnic
  • live music
  • food
  • event venue

• Montifalco Vineyard

  Ruckersville

  Small winery at the winemaker's home; Justin Falco trained in Northern California and the southern Rhone. Adults 21+ only.

  • dog-friendly
  • picnic

• Hardware Hills Vineyard

  Scottsville

  Started in 2007 as Thistle Gate, Fluvanna County's first vineyard; known for its sangria.

  • live music
  • food
  • picnic
  • event venue

Filter the trail

• Dog-friendly wineries36 of 44
• Wineries with food24 of 44
• Wineries with live music17 of 44
• Picnic-friendly wineries24 of 44
• Wineries with lodging9 of 44

How to do the trail without driving

Where to stay

Staying on the trail means no long drive after the last tasting. Towns with wineries on the Monticello trail:

• Hotels in Afton6 wineries in town
• Hotels in Barboursville5 wineries in town
• Hotels in Charlottesville10 wineries in town
• Hotels in Crozet4 wineries in town
• Hotels in Earlysville2 wineries in town
• Hotels in Faber1 winery in town
• Hotels in Free Union1 winery in town
• Hotels in Gordonsville1 winery in town

Lodging links may earn us a commission at no cost to you.

Best time to go

not listed (the trail's main festival, Monticello Wine Week, runs in late June)

Trail events

Dates as published by the trail. Confirm tickets on the official site.

Getting there

Nearest airports: Charlottesville-Albemarle Airport.