Musicians entertain guests with live music in winery tasting room

Published in the Sept. 18 issue of Morgan Hill Life:

By Marty Cheek

Photo by Marty Cheek Nate Castillo, 25, prunes a grape vine on the family property recently. The winery’s first effort was a Petit Syrah.

Photo by Marty Cheek
Nate Castillo, 25, prunes a grape vine on the family property recently. The winery’s first effort was a Petit Syrah.

Castillo’s Hillside Shire Winery started as a lucky accident. When he first started building his chateua-like house on an eastern hillside slope overlooking Morgan Hill, Jess Castillo never dreamed the enterprise would end up with him creating a vineyard and winery. But thanks to the machinery of government bureaucracy, the Castillo family got into the wine-making business.

“My dad is the builder and responsible for everything here,” said Jess’s son Nate Castillo, the winemaker as he showed off the lush garden and patio area surrounding the tasting room.

“Dealing with the county, getting permits can always be a hassle. After jumping through hoops, my dad was seven years in the project and he had done everything and was ready to break ground on the house. And then the county said he wasn’t in compliance with the Williamson Act. He said, ‘That’s cool, but I’ve never heard of that. You’ve known what I’ve been doing since the beginning but no one has told me about it.’”

Learning that the Williamson Act is a state law providing relief of property taxes to owners of farmland and open-space land in exchange for a 10-year agreement that the land will not be developed, the Castillo family decided to plant grapes on the hillside cradling their home. They contacted Gene and George Guglielmo, family friends who operate a winery down the road, and asked what vines they should plant.

“They told us, ‘Petite Syrah, because it’s good for the area and it’s a blending grape so if you mess it up, you can always do something with it,’” Nate said.

So one weekend, 12 men planted 3,900 vines on the hill. “It was ridiculous,” Nate said, recalling the arduous task he faced when he was a high school junior. “I did most of the vines on the top. I was wearing football cleats and everyone else was slipping and sliding.”

The first yield of their grape crop provided enough fruit for about two barrels of wine. The Guglielmo Winery instructed the family on how to turn the grapes into vino, and also provided equipment including its bottling line.

“We had this wine, we were giving it out to our friends and they we’re saying, ‘Jess This is good stuff, you should sell it,’” Nate recalled. “Gene and George tasted it and said, ‘Hey, this is pretty good. You’re not even Italian, you’re Mexican. Not too bad for Mexicans,” he added with a laugh at the joke.

After graduating from high school, Nate started learning how to make wine. At age 25, he is a level two sommelier. “I’ve always been working at vineyards and helping make wine,” he said. “I didn’t know what I wanted to learn. Oenology wasn’t for me. I was terrible at chemistry and I still am. I didn’t know what a sommelier was but when I found out what it was, I said, ‘That’s the school that I want to go to.’ And that taught me a lot.”


Morgan Hill’s accidental winery has undergone a remodel recently. Its garden, which has a newly-installed outdoor kitchen area, has been expanded to provide an area for 350 people suitable for weddings and other events. For winery members, there are occasional garden parties where jazz musicians play while people enjoy glasses of Castillo wine.

The Castillo family make sure that their enterprise is always entertaining for guests. “Anyone who comes in the tasting room, if they ask for someone to sing, then we have to,” Nate said. “My mom will sing opera and my sister will sing opera as well but usually she plays guitar. It’s like our thing.”


Location: 2215 Liberata Dr.
Hours: Saturday noon to 7 p.m.; Sunday noon to 5 p.m.
Contact: (408) 776-8200 or visit

Marty Cheek

Marty Cheek

Publisher at Morgan Hill Life
Marty Cheek is the publisher of Morgan Hill Life and Gilroy Life. He is also the co-author with Congressman Jerry McNerney of the book Clean Energy Nation: Freeing America From the Tyranny of Fossil Fuels.
Phone: (408) 782-7575
Marty Cheek