Wineries with live music on the Monticello Wine Trail

17 of the 44 wineries on the Monticello Wine Trail host live music.

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

• 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

• 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

• 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

• 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

• 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

• 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

• 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

• 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

• 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

• 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
• Picnic-friendly wineries24 on this trail
• Wineries with lodging9 on this trail

Wineries with live music on every trail we cover · All 44 wineries on the Monticello Wine Trail