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Bob’s Big Boy

Positioned in front of the Century theaters and down the street from the Winchester Mystery House, Bob’s Big Boy served up burgers and shakes from the mid-1960s to the late 1980s.  The Bob’s building, with its rock pillars and convex roofline, was designed by the Los Angeles based architectural firm, Armet and Davis, and is a prime example of “Coffee Shop Modern.”  Fortunately, when the folks at Flames took over from Bob, they did little to alter the building’s exterior.  Today, Flames Coffee Shop on Winchester Blvd. looks much like its predecessor, although one thing you’ll notice is that the original sign’s characteristic spike has been shortened.

Architect’s rendering of Bob’s Big Boy, San Jose, 1966
Image appears courtesy of Armet Davis Newlove, AIA Architects

Caravan Cocktail Lounge, San Jose, 1964










As a testament to its staying power, “OJ’s” in San Jose
has weathered the ups and
downs of the Valley’s
economy for over five decades.











The Caravan

In the early 1960s, you would have found the Caravan Lounge inside San Jose’s Greyhound bus terminal.  The San Jose Caravan used to be part of a chain, which included cocktail lounges in the Sacramento, Salinas and Santa Cruz Greyhound bus stations.  When Greyhound opted to part ways with the Caravan, original San Jose owner, Leo Chargin, decided to do the public a service and relocate the bar.  Consistently voted the Silicon Valley’s “Best Dive Bar” by Metro readers, the Caravan Lounge has been sitting at its current location, 98 S. Almaden Ave., since 1964. 


Original Joe’s Restaurant, San Jose, 1956

Original Joe’s 

Original Joe’s in San Jose opened to much fanfare in May 1956.  The restaurant was the brainchild of four business partners who wanted to bring a taste of San Francisco to San Jose: Louis J. Rocca, Louis J. Rocca, Jr., Arthur Tortore, and Anthony Caramagno.  As a testament to its staying power, “OJ’s” in San Jose has weathered the ups and downs of the Valley’s economy for over five decades.  The restaurant is still owned by the Rocca family and recently underwent a tasteful interior remodel.  This is one of the last remaining local venues for authentic “old school” dining, and the cocktail lounge is worth a visit too.


Stan’s Donuts, Santa Clara, c. 1956


Stan’s Donuts

The Mariposa Gardens Shopping Center opened on Homestead Road in Santa Clara in November 1956. As far as I can tell, Stan’s Donuts either opened with the shopping center or shortly thereafter.  Step inside Stan’s and you are stepping back in time.  The interior is classic 1950s, down to the long lunch counter with attached stools and the terazzo tile flooring.  The main reason to visit Stan’s, however, is not to view its design.  It’s to partake in some of the best donuts around – quite possibly, THE best.


The McDonald’s restaurant on Almaden Road in San Jose is an icon of mid-century American pop culture. The original building, designed by Stanley Meston around 1958 and constructed around 1960, is a boxy structure with a glass façade and red and white tile siding.  The roof is flat, sloped, and has been pierced by two giant gold arches.  Some years back, when pressure was on to update the restaurant, the original building was preserved and an addition, with a drive-through window, was constructed behind it.  The original McDonald’s now serves as the main dining area and the addition houses the kitchen.  This McDonald’s is one of the oldest in California and has been designated as eligible for city landmark status.

McDonald’s Restaurant, San Jose, c. 1960