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620 Oakville Cross Rd., Oakville, CA 94562, United States

Before he was elected San Francisco’s youngest-ever mayor, Gavin Newsom had found other ways to stir up the local establishment. His 1997 opening of PlumpJack Winery (cheekily named after Shakespeare’s Henry IV rogue Sir John Falstaff), raised lots of eyebrows in the wine-growing community: who was this new kid, with the audacity to release his inaugural Cabernet Sauvignon in a screw-cap bottle? Since then, though, the hullabaloo has died down, largely because it’s clear Newsom knows what he’s doing. The wines produced on the property—mostly Cabs, but also Syrahs, Merlots, and Chardonnays—have won several awards; try them yourself in the property’s nouveau-medieval tasting room.

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PlumpJack Winery

Before he was elected San Francisco’s youngest-ever mayor, Gavin Newsom had found other ways to stir up the local establishment. His 1997 opening of PlumpJack Winery (cheekily named after Shakespeare’s Henry IV rogue Sir John Falstaff), raised lots of eyebrows in the wine-growing community: who was this new kid, with the audacity to release his inaugural Cabernet Sauvignon in a screw-cap bottle? Since then, though, the hullabaloo has died down, largely because it’s clear Newsom knows what he’s doing. The wines produced on the property—mostly Cabs, but also Syrahs, Merlots, and Chardonnays—have won several awards; try them yourself in the property’s nouveau-medieval tasting room.