Escape to Eastwood



The History of the Blue Boar

Our blue boar first appeared in a painting by D. Alan Eastwood presented to his daughter, our cofounder, for her 10th birthday. The blue boar is the perfect Eastwood mascot – a magical creature and forest guardian. A surprisingly peaceable animal, the blue boar symbolizes courage, honesty, and fixity of purpose. According to legend, the blue boar is known for evading death and sharing his cloak of protection with loved ones, dreamers, and mythical kings embarking on enchanted quests. 

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A Food & Wine Destination on the Monticello Wine Trail

In the heart of Virginia’s Wine Country, enjoy award-winning wines and ciders in a beautiful atmosphere along with a delicious menu of shareable items + small plates in The Barn, fire-grilled snacks and entrees from our food truck, live music, events & more.

See our calendar for upcoming music and events at the winery.

Award Winning Wines

Our wines received four gold medals and four silver medals in the 2022 Virginia Governor’s Cup. 

Enjoy our four gold medalists in a tasting flight at the winery or order the Gold Medal Bundle to enjoy at home.

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Upcoming Events & Recent News

Red Wines of the Monticello AVA

Wine & Country Life spoke to Charlottesville wineries making award-winning red wines during the Red Wine Showcase at Eastwood Farm and Winery in April. Read the Article

Monticello White Wine Showcase

Mark your calendars for Friday, August 5. We are delighted to announce that we will be hosting the Monticello Wine Trail White Wine Showcase from 6-8PM. Tickets will go on sale soon.

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Join the NEW
Eastwood Wine Club

The Eastwood Wine Club just got some exciting new upgrades. June allocations are available for pickup now through the end of July. 

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Thank you for leaving us a review!
Visited Eastwood for the first time recently and it was wonderful. There are two parts to this winery and each has its own parking lot. There is the upper tent area with multiple picnic tables that is outdoors. There is also some uncovered patio-esque seating up there not under the tent. We went on a Saturday and there was also live music and a food truck.
Jasmine C.
Google Review
This place caught my attention because of how many Governor's Cup medals they won in 2022. The tasting room is spacious and comfortable. I tried the Governor's Cup flight. Really enjoyed the Meritage and Cabernet Franc. Excellent charcuterie plate available. They were hosting music bingo while I was there. The burgeoning Virginia wine industry is so exciting.
Dominic C.
Google Review