Chicago-California Dreams Pt. 1: West Oakland Train Station

Despite living there, I’d never considered the historic connection between the Bay Area and Chicago. After all, a huge geographical distance separates these regions. Plus, what would hard-working, gritty, flat and super-sized Chicago have anything to do with easygoing, wealthy, hilly, super liberal San Francisco? A historic train station can belie this presumption.

landscape architecture oakland california frederick law olmsted
Hills of cemetery designed by Frederick Law Olmsted in Oakland. San Francisco is in the background.

Oakland Train Station

Just across the Bay however, Oakland, California has always had ties to Chicago through the railroads. 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). 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. This train station was the terminus for the transcontinental trains from Chicago from 1912-1994.

Once a thriving community surrounding a bustling train depot, today West Oakland is notoriously dangerous. The construction of highway in the 1950’s isolated it from the rest of the Bay Area. Shortly after, the laying of the BART train tracks in the 1960s only further isolated it.

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.

West Oakland

Along the way, I passed historic homes that looked like something out of a Sears kit. The knobby accents and curly-q carvings seem Sears-y. Their size and architectural details are much more modest than the San Francisco ilk. They are just little cottages crammed together with perhaps a tiny patch of yard. A lot of Pullman train porters lived here, which we’ll talk about in Part Two of these California blog posts. I walked by little house after little house, and then suddenly, there was a giant expanse before me.

16th street train station Oakland Chicago history
16th Street Station, Oakland, California. See the elevated train tracks behind.

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. The wide open overgrown pavement in front of it further makes the building seem like a lonely relic. It was likely once used for pick-ups, drop-offs, streetcars, and buses, but it’s very lonely today.

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. This building feels like a void. Especially when you imagine the amount of people who arrived here from the East looking to make their California dreams come true.

Sadly Abandoned

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. Both train stations have giant sweeping arches on the exterior that clue you in to the high ceilings inside. 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. Today the waiting room walls inside 16th Street Station are spattered with graffiti.

oakland architecture train station chicago railroadsWhile 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. A housing development called “Central Station” plans to bring in condos, town homes and lofts. 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.

— Amanda Scotese, Executive Director


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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