Winery

Chiswell Farm & 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.

Chiswell Farm & Winery is a winery in Greenwood, Virginia, part of the Crozet & Western Albemarle area of Charlottesville wine country. Amenities include outdoor seating, weddings. There are 5 upcoming events on the calendar — see the full list below, or browse more events in the area on the events calendar. Explore more of Crozet & Western Albemarle.