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Discover Chiswell Farm & Winery | Chiles Family Orchards

Welcome to Chiswell

Greenwood, VA

A historic Jeffersonian estate nestled in the Virginia countryside, Chiswell Farm & Winery invites guests to delight in locally-crafted vintages, panoramic views, and warm hospitality.

Chiswell welcomes guests ages 21+

Aerial view of Chiswell Farm & Winery
Small group smiling with wine tasting flight

October is Virginia Wine Month

This year, we continue to celebrate the Monticello AVA’s honor of being named Wine Enthusiast’s Wine Region of the Year. Visit us any day from 11 AM–6 PM to toast the vineyards that make our state’s wine so special!

Crown Club

Crown Club

Our Chiles Family Orchards wine and celebration membership is about sharing the fruits of Virginia Wine Country with a tight-knit community.

Award-winning Chiswell Wines

Award-winning Wines

We are proud to announce that four of our wines received silver medals in the 2024 competition season!

Virginia Governor’s Cup medal winners include the 2021 Chardonnay, 2021 Petit Manseng, 2021 Meritage, and 2021 Cabernet Sauvignon. Our Chardonnay and Meritage also earned silver medals in the Monticello Cup!

From the Blog

Mother, father, and son drinking wine at Chiswell

Summer Wine Pairings

Wine and food are a pair as old as time. Each is better with the other—especially when you intentionally choose what’s on your plate and in your glass. In fact,…

We look forward to your visit!









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