Festival weekend planner
Monticello Wine Week — 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
Monticello Wine Week
Festival day — arrive early to avoid the lunchtime crowd. Insider tip: 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.
- Day 3
Wine country day in Virginia
Use the third day for a single winery visit (booked ahead) and a long lunch at one of the regional addresses below before heading home.
Where to stay
Three angles for the festival window. Festival hotels book out 6+ months in advance — apartments are the contingency when the main shortlist is sold out.
- Hotels in Charlottesville
Live inventory around the festival window — 2 adults, all star ratings.
- 4–5 star options near Charlottesville
Higher-end shortlist when you want the milestone weekend treatment.
- Apartments in Charlottesville
Self-catering option — useful when festival hotels sell out 6+ months ahead.
Booking.com links — we may earn a commission. We never recommend hotels we wouldn't use ourselves.
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
- Mid-range daily budget
- ~€180/day for two
- Festival site
- Visit official site
Insider tip
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.
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 →