Wine Events & Festivals

Festivals, barrel tastings, harvest events, and vineyard experiences — sorted by what's happening soonest.

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Monticello Wine Trail Wineries, Charlottesville

🎟 From $45

CharlottesvilleHarvest

Monticello Wine Trail Harvest Celebration

October 10–11, 2026

A weekend harvest celebration across the Monticello Wine Trail in Charlottesville, VA — 30+ wineries open for barrel tastings, grape stomps, and fall pairings.

From $45

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