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Wine Festivals in Virginia 2026

7 wine festivals across Virginia — from harvest celebrations to destination food-and-wine events.

Worth the Trip

Festivals worth travelling to Virginia for.

Tasting

Virginia Wine Expo

Richmond, United States$45-$1505K

A nine-day celebration of Virginia wine held at Richmond's spectacular Main Street Station, featuring 24 events including walk-around grand tastings, education seminars, spirit pairings, and sparkling wine celebrations. The 15th annual expo spotlights 370+ wines and 160 spirits from Virginia and international producers, cementing Richmond as a serious wine destination. An exceptional platform to taste the full depth of Virginia's winegrowing regions.

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Tasting

Monticello Wine Week

Charlottesville, United States$20-$755K

A focused week-long immersion in the wines of the Monticello AVA, with 40+ winery open houses, barrel tastings, educational seminars, and special events across Charlottesville and Albemarle County. Less ticketed festival and more wine trail exploration framework, Monticello Wine Week offers direct access to winemakers pouring library wines and limited releases not available year-round. The ideal time to discover Thomas Jefferson's wine-growing legacy in depth.

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Tasting

Taste of Monticello Wine Trail Festival

Charlottesville, United States$40-$1203K

Monticello Wine Week transforms Charlottesville into a celebration of Virginia's most prestigious wine region for six days, with tasting events, winery open houses, and the signature Grand Tasting at Ting Pavilion. Surrounded by 40+ acclaimed wineries in Thomas Jefferson's historic home county, the festival blends history, culture, and world-class Viognier, Cabernet Franc, and Petit Verdot. The rolling Albemarle countryside in late June is one of America's most beautiful wine backdrops.

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2026 Calendar — All Virginia Wine Festivals

Every wine festival in Virginia, organised by month.

Insider Tips

Monticello Wine Week

Plan 3 days minimum — the trail has 40+ wineries and many have exclusive week-only experiences. The Monticello Cup Awards dinner is the prestige event of the week.

Taste of Monticello Wine Trail Festival

Use the week as a self-guided winery tour — most of the 40+ trail wineries run special events and barrel tastings during the festival week.

LoCo Wine Festival

Your ticket includes a souvenir glass and tastings from all winery partners — meet the winemakers, they're typically on-site and love to talk.

Purcellville Wine & Food Festival

The festival weekend is ideal for booking a tasting room circuit in the surrounding Loudoun wine country — most wineries extend special offers to festival visitors.

Virginia Wine Expo

The Sunday Locals Walk-Around is the most relaxed and most Virginia-focused session — ideal for discovering emerging producers without the crowd.

Coastal Virginia WineFest (CoVa WineFest)

Sunday tickets are cheaper and the floor is less crowded — ideal for slower, more conversational tastings with the winery reps.

Shenandoah Valley Wine Festival

The museum entry is included — give yourself time to walk the Gardens of Glass before the wine crowd arrives. Advance tickets are $5 cheaper.