Winery
Chiswell Farm & Winery is part of the Chiles Family Orchards, set on a historic Jeffersonian estate in the Virginia countryside in Greenwood, near Crozet on the Monticello Wine Trail. The winery invites guests ages 21 and over to enjoy locally crafted wines, panoramic countryside views, and warm hospitality. Its wines have earned strong recognition, including six awards in the 2026 Virginia Governor's Cup with gold medals for the 2023 Meritage and 2023 Merlot and silver medals for several other vintages. Visitors can build their own tasting flight or choose from recommended flights, including a Governor's Flight of recent award winners, and sip seasonal specialty drinks such as a strawberry citrus spritzer. Open most days of the week, Chiswell also offers the Crown Club membership for those who want to share in the Virginia wine country experience throughout the year.
Celebrate summer at the Virginia Sunflower Fest at Chiswell Farm in Greenwood, VA, just outside Charlottesville! Wander through vibrant sunflower fields, capture unforgettable moments with friends & family, and cool off with our refreshing drinks! From sunflower picking to stunning views, it's the ultimate summer escape. Runs Thursdays–Sundays from mid-July through early August, 10 AM–6 PM.
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On the third Thursday of each month, Rachael Karpo is hosting music trivia night at Chiswell — and it's free to attend!
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Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
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Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
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On Saturday, 8/8 at 7 PM, Crown Club members will be enjoying light plates freshly made from Chiles Peach Orchard's seasonal harvest.
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On the third Thursday of each month, Rachael Karpo is hosting music trivia night at Chiswell — and it's free to attend!
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Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
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Spend your holiday enjoying wine and live music at Chiswell! Local acoustic musicians will perform from 1–4 PM on Monday, September 7, 2026.
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On Saturday, 9/12 at 6:30 PM, Crown Club members will take a pre-harvest look at the crop before engaging in some old-fashioned grape stomping!
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On the third Thursday of each month, Rachael Karpo is hosting music trivia night at Chiswell — and it's free to attend!
More Info
Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
More Info
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
More Info
Crown Club members and their guests will be guided through these sweet pairings by Gearharts Fine Chocolates. Advance registration is requested.
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On the third Thursday of each month, Rachael Karpo is hosting music trivia night at Chiswell — and it's free to attend!
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Crown Club members and guests are invited to solve Chiswell's murder mystery, starting at 5:30 PM on Saturday, November 14.
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Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
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Members of our wine club and their guests will be exchanging gifts during a special holiday celebration on Saturday, December 12!
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Join us for live music, Christmas cookies, and traditional mulled wine at our holiday open house on Friday, December 18.
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