Picnic-friendly wineries on the Monticello Wine Trail

24 of the 44 wineries on the Monticello Wine Trail welcome picnics or have picnic areas.

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

• 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

• 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

• 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

• 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

• 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

• 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

• Michael Shaps Wineworks

  Charlottesville

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

  • picnic

• 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

• 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

• 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

• 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

• 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

More ways to plan the Monticello trail

• Dog-friendly wineries36 on this trail
• Wineries with food24 on this trail
• Wineries with live music17 on this trail
• Wineries with lodging9 on this trail

Picnic-friendly wineries on every trail we cover · All 44 wineries on the Monticello Wine Trail