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In my years living in San Francisco, I never considered the possibility of much historic connection between the Bay Area and Chicago. Just across the Bay however, Oakland, California has always had ties to Chicago through the railroads. Once a thriving community surrounding a bustling train depot, today West Oakland is notoriously dangerous. Along the way, I passed many of those homes that may have been made entirely out of a Sears kit with knobby accents and curly-q carvings. Designed by architect Jarvis Hunt, who had his offices in the Monadnock Building for much of his architectural career, this stone behemoth of a building seems to patiently wait at the far edge of West Oakland, with chopped-off, elevated train tracks in the back suspended as though in the off chance a train might someday return.
While I did not get to scale the barbed wire fence to enter the Oakland train station, I imagine the interior somewhat similar to Hunt’s Kansas City train station, which I have been through and is very much active today. While a quick surf of this West Oakland train station on the internet might give you the idea that the area has undergone major redevelopment, but in reality the plans for a museum, beer garden, charter school, restaurant and urban farm need at least $30 million to happen. If you manage this site and have a question about why the site is not available, please contact us directly.
With such distance between these two cities, what would hard-working, gritty, flat and super-sized Chicago have anything to do with easygoing, wealthy, hilly, super liberal San Francisco?

I first read about these economic and social ties in American Babylon, a must-read for anyone curious about Bay Area history, black history, and American city development (it’s pretty dense though – let’s say it’s a “must-skim” at least).
It has become somewhat isolated from the rest of the Bay Area with the construction of the highway in the 1950s and shortly after, the laying of the train tracks in the 1960s for the commuter transit system of BART. Their size and architectural details are much more modest than the San Francisco ilk, with many as just little cottages crammed together and perhaps a tiny patch of yard.
The wide open overgrown pavement in front of it, likely once used for pick-ups and drop-offs and streetcars and buses, further makes the building seem like a lonely relic. Both train stations have giant sweeping arches on the exterior that clue you in to the high ceilings inside. Well, other than the Sears catalog ornamentation of the early 1900s that you find all over those iconic Victorian homes, you won’t find much overlap in the histories of Chicago and San Francisco.
With my recent trip to California to see friends and conduct some top-secret tour research for Chicago Detours, I got a chance to uncover some of this history firsthand with a visit to West Oakland’s old and abandoned 16th Street train station.
I would never let my father know I did this, but a few days ago I left downtown Oakland on foot, walking alone – during daytime of course – to get to the train station.
A lot of these homes housed Pullman train porters, which we’ll talk about in Part Two of these California blog posts.

Other examples of historic architecture in West Oakland, such as former factories and warehouses, elicit vitality as they have been taken over by artists, musicians, religious groups and non-profits. The cathedral-like lofty ceilings you find in the architecture of historic train stations bring out that expansive feeling of the excitement of heading off to a new land, perhaps to an entirely new life.
Owned by a non-profit housing organization called Bridge, for now the 16 Street Station crouches in the shadow of the elevated highway, awaiting a future era. This train station was the terminus for the transcontinental trains from Chicago from 1912-1994. I walked by little house after little house, and then suddenly, there was a giant expanse before me. This building, which has likely hosted more visitors than all West Oakland warehouses combined, feels like a void when you imagine the amount of people who have arrived here from the East looking to make their California dreams come true.

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