Festival weekend planner
Taste of Monticello Wine Trail Festival — a 3-day weekend in Virginia
22–28 June. Charlottesville, United States. 20 min from the airport.
The weekend, day by day
- Day 1
Arrive in Charlottesville
Land at CHO — Charlottesville Albemarle Airport, settle in and walk the old town in the afternoon. Light dinner near your accommodation — save your appetite for the festival day.
- Day 2
Taste of Monticello Wine Trail Festival
Festival day — arrive early to avoid the lunchtime crowd. Pace yourself across the tastings and break for a long lunch mid-afternoon.
- Day 3
Wine country day in Virginia
Use the third day for a single winery visit (booked ahead) and a long lunch before heading home.
Where to stay
- Hotels in Charlottesville
Live availability around the festival dates. Festival hotels book out 6+ months ahead, so check early.
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One winery worth a detour
Barboursville Vineyards
Thomas Jefferson's vision of Virginia wine fulfilled — world-class Bordeaux blends and Italian varieties on a historic plantation most oenophiles overlook.
- Address
- 17655 Winery Rd, Barboursville, VA 22923, USA
- Appointment
- walk-in
- Tasting price
- USD 15 · Flight of 6 wines
- Website
- Visit
Where to eat
Ox-Eye Vineyards Cellar Door
$$Shenandoah Valley winery with cheese and charcuterie boards celebrating Virginia's artisan food scene
Must try: Virginia ham and biscuits
More dining picks in Virginia →Practical
- Nearest airport
- CHO — Charlottesville Albemarle Airport
- Festival site
- Visit official site
Insider tip
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.
Want a longer trip than the festival weekend?
The milestone-trip planner builds a 3–10 day Virginia itinerary with accommodation, tours, and pacing options.
Plan a Virginia trip →