Chiswell Farm & Winery

Owned by the Chiles family of Carter Mountain Orchard, grape growers for 30+ years; wines made by Michael Shaps and Matthieu Finot. Adults 21+ only, no dogs.

On the Monticello Wine Trail · checked October 1, 2026 on the winery’s own website

Town
Greenwood, Virginia
Address
430 Greenwood Road, Greenwood, VA 22943
Phone
(434) 252-2947
Tasting
Build-your-own flight of 4 wines (price not listed); Reserve Tasting $30 per person by reservation
Reservations
Walk-ins welcome
Hours
Mon-Thu 11am-6pm, Fri 11am-8pm, Sat 11am-7pm, Sun 11am-6pm
Also
food

Visit without driving, stay nearby

Visit Charlottesville lists local tour and transportation companies that run multi-stop days on the Monticello Wine Trail, plus a trolley, e-bike tours and horseback rides between some vineyards. A local tour company notes the wineries are spread across rural Albemarle County and the trail is not walkable.

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Also in Greenwood and nearby

All 44 wineries on the Monticello Wine Trail

Sources

Details change. Confirm hours and fees with Chiswell Farm & Winery before you go. Own this winery and see an error? Email hey@americawinetrails.com.