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Back to Virginia Wine Month — October

Festival weekend planner

Virginia Wine Month — October — a 3-day weekend in Virginia

October. Charlottesville, United States. 20 min from the airport.

The weekend, day by day

  1. Day 1

    Arrive in Charlottesville

    Land at Charlottesville-Albemarle Airport (CHO), settle in and walk the old town in the afternoon. Light dinner near your accommodation — save your appetite for the festival day.

  2. Day 2

    Virginia Wine Month — October

    Festival day — arrive early to avoid the lunchtime crowd. Pace yourself across the tastings and break for a long lunch mid-afternoon.

  3. 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.

We may earn a commission on hotel links.

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
Read the full Barboursville Vineyards guide →

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
Charlottesville-Albemarle Airport (CHO)
Festival site
Visit official site

Insider tip

Focus on the smaller producers along the Monticello Wine Trail's eastern quadrant (Pippin Hill, Trump, Barboursville)—they host intimate October dinners not advertised statewide. Many Virginia wineries waive tasting fees during Wine Month if you call ahead, and harvest events often include barrel-sample futures at 20% discounts.

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 →