8 Wine Festivals in Virginia to Put on Your Calendar This Fall

By Robin Shreeves

September 29, 2022

Check out this list of wine events happening across the commonwealth this season.

Fall is the busiest time of the year for Virginia wineries, as that’s when the harvest comes in and winemaking is at its peak. It’s a wonder that wineries have the time to do much else this season aside from turning grapes into wine.

Yet, in addition to welcoming wine lovers to their tasting rooms, they also go into festival mode, catering to wine connoisseurs and newbies alike. 

Virginia Wine has a list of events that you can search by category, but we’ve rounded up a sampling of wine festivals in 2022 throughout the state of Virginia to get you started on your search.

Powhatan’s Annual Festival of the Grape

8 Wine Festivals in Virginia to Put on Your Calendar This Fall
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Location: Historic Courthouse Village, 3860 Old Buckingham Road, Powhatan

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Celebrate the 19th Annual Festival of the Grape sponsored by the Chamber of Commerce held at Powhatan’s historic Courthouse Village in Powhatan County. There’s much more than wine at this family-friendly party in the streets. Over 30 Virginia wineries, distilleries, cideries, meaderies, and craft breweries will be pouring at the event. There’ll be live music, over 100 craft vendors, and at least 10 food trucks. 

Weather permitting, the festival will be held on Saturday, Oct. 1 from 11 a.m. to 6 p.m. Advanced tickets for youth ages 13-20 are $20. Tickets for ages 21+ are $25. All tickets are an additional $10 the day of. 

Wind Vineyards Fall Harvest Festival

8 Wine Festivals in Virginia to Put on Your Calendar This Fall
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Location: 5178 Richmond Tappahannock Highway, Tappahannock

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Wind Vineyards in Essex County fall fests it up the first four Saturdays and the final Sunday of October. The Second Annual Fall Harvest Festival is a month-long family-friendly event with wine, games, hay rides, bounce houses, carnival rides, vendors, food trucks, live music, pumpkin painting, and a monster truck display. 

The festival is held on Saturdays throughout October from 11 a.m. to 6 p.m. Tickets are $10 for children 3-12 and $13 for ages 13 and up. 

Fall Wine Festival and Sunset Tour at Mount Vernon

Location: East Lawn, 3200 Mount Vernon Memorial Highway, Mount Vernon

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This festival held at George Washington’s Mount Vernon in Fairfax County allows guests to sample unlimited wines from 20 of Virginia’s outstanding wineries. Bring a blanket or small lawn chairs and relax on the East Lawn overlooking the Potomac River while Lady and George Washington wander the grounds and greet guests.. Food is available for purchase. Or reserve a VIP table for up to 12 people that includes three bottles of Mount Vernon house wine, food, and private waiter service. 

The festival runs from Oct. 7-9 from 6 p.m. to 9 p.m. Tickets for members of Mount Vernon start at $43 and at $49 for the general public.

Rebec Vineyards 30th Annual Virginia Wine and Garlic Festival

8 Wine Festivals in Virginia to Put on Your Calendar This Fall
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Location: 2229 N. Amherst Highway, Amherst

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The motto of this two-day gastronomical pairing of wine and garlic is “It’s Chic to Reek.” Held at Rebec Vineyards in Amherst in Amherst County, 10 guest wineries and cideries will be on site for the family-friendly 30th Annual Virginia Wine and Garlic Festival. Four stages will host continuous entertainment and more than 150 vendors with arts, crafts, and garlicky foods—like fresh-baked garlic braids and juicy garlic burgers—will set up their booths. It’s going to be a “Stinkin’ Good Time!”

The festival runs on Oct. 8 & 9 from 10 a.m.-5 p.m. Wine tasting tickets start at $28 and non-wine tasting tickets start at $20.

Caledon State Park Art & Wine Festival

Location: Caledon State Park, 11617 Caledon Road, King George

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Held by the Friends of Caledon, the Caledon State Park Art & Wine Festival is a regional wine-tasting experience with local artisans and food vendors. For two days, the King George County park hosts this family-friendly and on-leash, pet-friendly event that celebrates wine, food, art, and music. 

The festival runs on Saturday, Nov. 5 from 10 a.m. – 5 p.m. and Sunday, Nov. 6 from 10 a.m. – 4 p.m. Admission is free for non-tasters and children Tickets for tasters are $20 online and $25 at the gate; parking is $5 per cash per vehicle.

Rosemont’s 13th Annual End of Harvest Celebration

Location: 1050 Blackridge Road, LaCrosse

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The Annual End of Harvest Festival is held each year at Rosemont Winery in LaCrosse in Mecklenburg County. Bring a picnic blanket and enjoy wine tastings, food vendors, live music, grape stomping at 2 p.m., activities for the whole family, and a family photo setup opportunity. 

The festival is held on Oct. 15 from 11 a.m.-6 p.m. Admission is free. Tastings are $10 and include a souvenir glass. 

Town Point Virginia Fall Wine Festival

Location: Town Point Park, Downtown Norfolk Waterfront


One of Hampton Roads’ most anticipated wine festivals, the Two Point Virginia Fall Wine Festival is held at Town Point Park along the Downtown Norfolk Waterfront. Over 30 wineries, cideries, and meaderies will pour their locally crafted drinks while live music fills the air. Food and craft vendors will be on hand, too.

The festival is held on Oct. 15 & 16 from 11 a.m. – 6 p.m. General admission tickets are $30. Tickets with wine tastings are $40.

Two Up Wine Down

8 Wine Festivals in Virginia to Put on Your Calendar This Fall
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Location: Jefferson School City African American Heritage Center, 233 4th St. NW, Charlottesville

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Two Up Wine Down, an inclusive community-focused Virginia wine festival, spotlights BIPOC wine professionals, enthusiasts, and allies. Blenheim Vineyards’ Oenoverse Club will play host while members of the Veraison Project pour tastings of their favorite Virginia wines and also share perspectives and conversations with guests.

The all-ages festival is held on Sunday, Oct. 23 from 3 p.m. – 6 p.m. Tasting tickets are $15 until Oct.1 and will increase to $20 after the 1st. Tickets are $25 at the door. Wines by the glass or bottle will also be available for sale.

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