A serious illness in 2009 at age 39 changed Shannon O’Shaughnessy’s perspective on what it means to be alive. That pivotal event led her to where she is now — flying vintage airplanes, driving fast cars and making wine.
“Prior to having kids, I was a dive master, an avid hiker; I did all of those things. There was nothing better I’d ever done in my life than being a mother, but I’d lost myself in that a little bit,” O’Shaughnessy says, pointing to a life-changing leap off a tall rock in a river between surgeries that changed her point of view. “I made a commitment that I was going to do the things I hadn’t done. Am I going to take the shortcut? Or am I going to figure out a way to make it meaningful and live my life with intention and teach my kids to do it that way, too.”
Her dad had already instilled a fondness for planes — she still remembers sitting with her two sisters in the back of his plane with their Barbie dolls — and the German cars the family admired. But her parents — moving from Minneapolis to Napa and purchasing property in Oakville in the 1990s — instilled something else: a Midwestern sense of hard work as they built up the venerable O’Shaughnessy Estate Winery from nothing, and where Shannon began to experience “the valley and the magic of what it is.”
After her illness, O’Shaughnessy returned to flight school — she had quit earlier in life — and at 40 finally earned her pilot’s license. “When you get in the plane there isn’t any space, especially when you’re learning, for anything else in your mind,” she says.” All you are is fixated on one thing, and the satisfaction of working hard to be able to accomplish something.”
O’Shaughnessy continued with that focused mindset, purchasing a Coombsville property then owned by acclaimed winemaker Andy Erickson and his wife, Annie Favia, that featured organic, dry-farmed sauvignon blanc vines planted by the couple. “I got wind that the house might be for sale and bought it the next day,” she says. “When I bought that in 2014, it kind of opened up the winemaking possibility again, because now I had an anchor piece of property for making wine.”
And just two years later, the limited-production, boutique label, Aileron Estates — named for the hinged surface on the edge of an airplane wing — was born. Soon after, her mom gave her an evergreen contract to buy cabernet sauvignon from the family’s Rancho Del Oso vineyard on Howell Mountain, and she purchased another cabernet sauvignon vineyard boasting rocky red soils in 2019 at the top of Napa’s Atlas Peak AVA.
About Howell Mountain O’Shaughnessy says, “That was meaningful to me because it was the piece of property that I was really active in when we bought it, cleared it, planted it and started building the winery during the years that I was there.”
And now she is able to combine two of her favorite things. Just this year O’Shaughnessy partnered with Vintage Aircraft Company in Napa’s Carneros region on a program where their pilots would take guests up in World War II vintage Boeing PT-17 Stearman biplanes followed by a tasting at her estate (the program was so popular that it became unwieldy and is no longer offered but will be coming back in some form in the future).
“These planes are historic and majestic and slow, but unbelievably powerful. It’s this visceral thing. This giant radial engine creates all of this wind, then all of this noise,” she says about the experience. “I feel almost a little opportunistic taking people on this really cool experience and then saying, ‘taste my wine.’ If you love the biplane experience, then you’re going to think the wine tasting is pretty cool, too.”
And her passion for vintage cars has led to a new obsession: driving on a racetrack. “I’m a little afraid of how exciting I think it is to drive on a racetrack. Flying doesn’t seem overly risky to me, but driving on a racetrack might because I am so competitive: ‘I can drive faster than that person,’” she says. As for vintage cars, O’Shaughnessy explains that the appeal is similar to that of a well-aged wine. “It’s a bit nostalgic. It is such a simple machine, but it’s miraculous what it is, what they had created that’s now 60 years old.”