Once a quiet dairy farm on the edge of San Mateo, California, the site of Hillsdale Shopping Center would grow into one of the most recognizable shopping destinations on the San Francisco Peninsula. From its sun-soaked, open-air roots in the 1950s to its glossy, two-story expansion in the 1980s, Hillsdale mirrored the rise of suburbia, mall culture, and regional retail identity.
Today, we look back at Hillsdale’s transformation—through archival detail and a classic 1950s postcard—with a few personal glimpses of what it was like to experience the center during its retail heyday.
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| Inside Hillsdale Mall in the 2010s, a decorative “H” pole near Macy’s serves as a subtle wayfinding landmark—part of the mall’s refreshed signage system enhancing navigation and brand identity. |
1954: A mall grows in San Mateo
When Hillsdale Shopping Center officially opened in November 1954, it marked more than the debut of a shopping plaza—it reflected California’s postwar suburban boom. Developed by David D. Bohannon on what had once been a dairy farm, the center was anchored by a brand-new Macy’s, which opened on November 19. But Hillsdale’s retail story actually began earlier, with a standalone Sears that opened nearby on March 22, 1951, serving as the initial retail draw long before the mall was built. For those in the East Bay, Bohannon's name might also sound familiar—he was the developer behind San Lorenzo Village.
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| Architectural rendering of the future Hillsdale Shopping Center in San Mateo, published in May 1952. Designed by architect John Savage Bolles, the plan divides the mall into three sections, separated by Hillsdale Boulevard and 31st Avenue—illustrating the scale and ambition of this postwar suburban retail development. |
Designed as an open-air shopping center, the mall featured wide walkways, palm-lined paths, and easy car access. It was created for a mobile, suburban lifestyle where retail and convenience met curbside.
I first learned about Hillsdale’s early development in a CSM History of San Mateo County class—while everyone else was nodding off during the land-grant portion, I perked up the moment the teacher mentioned the mall.
1950s postcard: Hillsdale in its mid-century prime
This vintage postcard, likely from the late 1950s, captures the optimism of the era: a full parking lot of chrome-trimmed cars, bold signage, and clean-lined modern architecture beneath blue skies. It’s a portrait of retail promise—shopping as leisure, the mall as a place to see and be seen.
Though I didn’t grow up during this era, seeing this postcard decades later helped explain why Hillsdale had always felt iconic to me. It wasn’t just another mall—it had history.
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| Vintage postcard of Hillsdale Mall in San Mateo, circa late 1950s, featuring mid-century architecture, a bustling parking lot, and palm trees. |
The back of the card reads "Hillsdale, California. Heart of the San Francisco Peninsula. Located on the famous 'El Camino Real,' just 20 miles from San Francisco. This beautiful shopping center offers the newest and most modern shops and stores."
1960s–1970s: expansion and evolution
As San Mateo and the Peninsula continued to grow, Hillsdale expanded to meet the demand. Over the years, new stores were added, including The Emporium in September of 1962. Still open-air, the mall remained a go-to destination—but by the late 1970s, it was clear that consumer preferences were shifting.
The competition was heating up. Enclosed malls were taking over—places like Tanforan and Serramonte Mall drew crowds with climate control, escalators, food courts, and movie theaters. Then came talks of building a new mall in San Mateo in 1972. Hillsdale needed to evolve or risk being left behind.
1981: a major overhaul brings Hillsdale indoors
In 1981, Hillsdale embarked on its most ambitious redevelopment: transforming the open-air plaza into a fully enclosed, two-level mall.
The expansion added:
A new Nordstrom, the first in the region, as a key anchor
A new two-level Mervyn's
A large food court with then-cutting-edge design
Parking decks and updated architecture with skylights and glass atriums
For many locals—including me—this was the version of Hillsdale that felt like the mall. I remember seeing the overhead promotional image in an ad and cutting it out, tacking it to my wall like it was a movie poster. Something about that rooftop layout and perfect symmetry felt cinematic.
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| 1981 Hillsdale Mall expansion ad showing the new Nordstrom and rooftop layout. |
Beyond retail: art, architecture, and the unexpected
What made Hillsdale unique wasn’t just the stores—it was the details. During the 1980s renovation, the mall kept the modernist sculptures originally installed in 1956 by Beniamino Bufano. These weren’t off-limits museum pieces; you could actually touch them.
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| Seal sculpture by Beniamino Bufano, crafted from red granite and displayed at Hillsdale Mall in San Mateo. Installed in 1956 as part of the mall’s original open-air design, the sculpture remains a charming example of Bufano’s stylized animal forms in public spaces. |
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| Penguin and two baby penguins sculpted in black granite by Beniamino Bufano, displayed at Hillsdale Mall in San Mateo since 1956 as part of a public art installation featuring animal figures across the shopping center. |
One of my favorite spots was the spiral staircase that led to Cost Plus Imports—a little below-ground enclave that felt like a secret passage. I’d go there for candy wrapped in edible paper and foreign snacks I didn’t understand but absolutely needed.
Hillsdale today: evolving, but still a landmark
Hillsdale has continued to evolve into the 21st century—adding a movie theater, new dining options, and an outdoor plaza in recent years. But its foundation was laid decades ago, by a bold suburban vision in the 1950s and a massive reinvention in the 1980s.
That 1950s postcard shows where it all began.
And even now, Hillsdale remains more than just a place to shop—it’s a part of Peninsula identity.
Related posts
- Exploring Hillsdale Mall in San Mateo – a look back at 1982 with the vintage directory
- Lost department stores: Emporium-Capwell (1896—1996)
- Lost malls: San Mateo Fashion Island (1981—1995)
Comments
Was Hillsdale once considered and marketed as a separate community from San Mateo? I've seen old maps that treated it as such. Was it always in San Mateo city limits or later annexed?
BTW, until the 1970's I think all Macys in the Bay Area had the 3333 ending on their phone numbers.
My memories of my History of San Mateo County class was that Hillsdale was marketed much like other large-scale developments of the time. For example, Westlake Village. Westlake, like Hillsdale, was ultimately annexed by the neighboring town (Daly City in the case of Westlake). If I'm right, Broadmoor Village was NOT annexed by Daly City and still remains unincorporated. Much like San Lorenzo in the East Bay and so on.
Scott
I recently found a great movie on the internet archive that is all about the Hillsdale Mall. The movie is called, "Shopping Can Be Fun: A New Concept in Merchansiding" and was filmed around 1957 - the time of this postcard.
http://www.archive.org/details/Shopping1957
I'd love to see more snapshots from the pre-enclosed era. I remember the Cost-Plus used to have a glass atrium over it's curved underground staircase, and there was a huge "Rainbow Records" across from what is now Good Guys.
Enjoy the flick!
For years I've searched for info on the wonderful old animatronic Christmas displays they would set up in down the middle of the mall... moving reindeer, waving dolls, sleeping santas, etc. They were in little building that kind of looked like glass gazebos.
They did away with them when the mall was modernized. Anyone know where they went? Who they were sold to?
When we first shopped at Hillsdale Mall:
1) The parking lots all were ground level.
2) The stores on the East end between Macys & Farmers market were not built yet. There was a walkway, but the construction site was boarded off, with small holes to watch the construction.
3) The old Sears store was not remodeled till the 60's, so looked older than the rest of the mall. The auto center was part of the main building.
4) The "farmers market" building was smaller. The grocery had seperate greengrocers, dry goods store, bakery & meat dept. The restaurant area doubled in size when the Emporium was built. On Sundays all the restaurants offered Sunday dinner for $1.
Does anyone know what was on the mall property BEFORE Hillsdale?
At Christmas I remember Sears had Winnie The Pooh stuff EVERYWHERE, but more so had out front a large Donald Duck playing a song that I believe was "Barnacle Duck The Sailor".
Was Melarts an "upscale" toy shop? My parents used to get my sister Madame Alexander dolls there. I would love to have one of those Corgi Batmobiles they sold.
Does anyone remember a store that you would enter through a curved or spiral staircase going underground and it seemed to sell a lot of 70s maybe early 80s crafty things, like burl wood clocks, macrame, etc.?
This was before the mall was enclosed, and before Cost Plus?
And I LOVED going down the slide at Melarts!
Thanks!
I would have been a kid at that mall from 1967 on.