Chestnut Oak Vineyard

Small-batch wines about 20 minutes from Charlottesville, served by the flight, glass or bottle.

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

Town
Barboursville, Virginia
Address
5050 Stony Point Road, Barboursville, VA 22923
Phone
(434) 964-9104
Tasting
Flights $15-$20
Reservations
Not listed
Hours
Fri-Mon 12-5pm
Also
dog-friendly · picnic

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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All 44 wineries on the Monticello Wine Trail

Sources

Details change. Confirm hours and fees with Chestnut Oak Vineyard before you go. Own this winery and see an error? Email hey@americawinetrails.com.