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Olivia Decker
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There was a time when Cupertino’s economy was fueled by prunes, cherries, plums, apricots and grapes; now it runs on Apples – as in Apple, Inc., the technology giant founded by Steve Jobs and Steve Wozniak that has been headquartered in Cupertino since 1977. Since then, as Apple has grown, so has Cupertino.

But Cupertino, with well over 100 years of history and a population of 60,000, is more than just a bedroom community for Apple. It’s a top-ten-happiest suburb in the U.S., according to Business Insider, and one of the most educated cities in the country according to Forbes Magazine. It’s a classic post-war American suburb trending upward to the point where it now appears on some publications’ lists of America’s wealthiest cities.

Cupertino incorporated on October 10, 1955 during the Santa Clara Valley’s first period of rapid expansion. Despite its 19th-century history, modern Cupertino is an entirely post-war suburb with no central downtown. Shops, restaurants and businesses, including Vallco, one of Silicon Valley’s first “destination” shopping malls when it was built in 1976, fan out from Cupertino’s historic town center, at the corner of Stevens Creek and De Anza Boulevards. In 1900, this was where a post office first wore the “Cupertino” name. Today it’s an always-busy crossroads lined with all manner of businesses, including big box retail stores and even bigger parking lots.

Stevens Creek Boulevard is where you’ll also find De Anza College, a two-year institution established in 1967 on the site of a winery owned by Charles A. Baldwin. Baldwin’s former mansion, known as “Le Petit Trianon,” also located on De Anza College property, today serves as the California History Center.

Despite – or perhaps because of — its decentralized configuration, Cupertino works hard to support its residents’ sense of community. The city manages a packed slate of events, including a monthly flea market on the De Anza campus, a weekly farmers’ market at Vallco, an annual harvest festival, a cherry blossom festival, a holiday tree lighting, several fun runs and a summer concert series held at Memorial Park, one of several public green spaces within the city limits.

And don’t think there’s no sense of history in Cupertino. Though its first subdivision, Monta Vista, is less than 70 years old, Cupertino grew quickly in the 1950s, giving it a notable collection of mid-century homes built by Joseph Eichler and Cliff May, the “father of the California ranch house.” Homes in Eichler’s Fairgrove Tract are a big draw to those caught up in the resurgence of the mid-century style, as is May’s Rancho Rinconada, a tract featured in Sunset Magazine’s 1955 feature “New Homes for Western Living.”

If there is one thing to know about Cupertino, it is that it does not stand still. The city’s mid-century homes are balanced by much newer housing developments, some containing very large and luxurious homes. Steven Creek Boulevard’s 1970s-era motif is contrasted by “Main Street Cupertino,” a once-vacant lot at the corner of Stevens Creek and Finch Avenue that is now a traditional pedestrian downtown, with shopping, restaurants, commercial space and a 120-unit live-work loft project.

Once a quiet expanse of fruit ranches, then the embodiment of 20th-century California suburbia, Cupertino continues to evolve and thrive as it leaps forward into the 21st.
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