Spend some time with the Long Lost Oakland puzzle and you’ll probably find yourself asking questions. Why is there a balloon floating over the city? What was that hotel with streetcars running through it? And what’s the story behind the cannery along the waterfront?
Those questions are part of what makes this image so interesting to spend time with. Adapted from the hand-drawn map created by artist T.L. Simons and East Bay Yesterday’s Liam O’Donoghue, our 500-piece Long Lost Oakland puzzle brings together buildings, transportation systems, wildlife, and landscape features from different periods of Oakland’s history. As you assemble it, familiar streets become starting points for discovering what came before.
We recently spoke with Liam about how the map came together, the stories tucked into its illustrations, and what happened when a project about Oakland’s past found a new audience around the puzzle table.
Listening to the People Who Make Oakland What It Is
Liam started East Bay Yesterday in 2016, drawing on a background in journalism and a growing desire to focus on the community where he lived. Oakland was changing quickly, and he wanted to record the experiences of longtime residents while helping newcomers understand the place they were making home.
He kept finding stories in everyday conversations. At gatherings, someone who had grown up in Oakland would share a memory that opened up an entirely new subject to explore. While the city’s sports teams and the Black Panthers had received considerable attention, he saw opportunities to tell more stories about everyday people, neighborhood life, and community organizing.
The podcast gave those people room to speak for themselves. Some of the elders Liam interviewed had never been asked to share their life stories before, and their response encouraged him to keep going. Over time, East Bay Yesterday expanded into radio, newsletters, presentations, and tours, creating more opportunities for people to exchange memories and ask questions.
A Map Inspired by the View Outside the Window
The idea for Long Lost Oakland grew out of changes Liam and T.L. Simons could watch from their own home. Roommates for ten years, they lived on Telegraph Avenue near downtown, where redevelopment was happening all around them.
Buildings came down, cranes arrived, and new structures rose. Liam, who often walked or rode his bike through the city, remembers how disorienting it could feel to pass a new building and struggle to recall what had occupied that spot only a short time earlier.
He wanted a physical, visual way to explore those changes. Working with Simons, he helped develop a map that brought different periods of Oakland’s history into one image. Researching it revealed how many times the city had already undergone rapid transformation, with each era leaving traces that still shape life here.
The map also became an invitation for people to share their own memories. At one presentation, Liam met a man in his nineties who remembered watching Amelia Earhart take off from Oakland Airport. Encounters like that connected historical research with people who had witnessed events firsthand.
The Stories Behind the Details
Ask Liam to choose a detail people might overlook, and he points to the Pacific Coast Cannery. A food-processing building might seem ordinary at first glance, but its founder, Lew Hing, played an important role in the lives of people arriving in Oakland.
After the 1906 San Francisco earthquake, Chinese survivors faced discrimination at official relief camps. Lew Hing provided food and shelter on the grounds of his West Oakland cannery. The building’s story opens into a much larger history of immigration, racism, entrepreneurship, and community support.
Elsewhere on the map, the Key Route Inn offers a glimpse of a very different journey through downtown. The hotel at Broadway and West Grand Avenue straddled electric streetcar tracks, allowing guests to board the Key System without leaving the building. Looking at its illustration can change the way you picture an intersection you’ve passed countless times.
Then there’s the City of Oakland balloon. Its 1909 launch was meant to celebrate Oakland’s rising prospects, with crowds gathering to watch it take flight. The trip ended with the balloon’s occupants bruised and battered after a rough landing. For Liam, the episode captures something about the cycles of ambition, growth, and setbacks that recur throughout the city’s history.
These are the kinds of stories that reward a closer look. A building, a vehicle, or an animal that first catches your eye because of its shape or color can lead you into a subject you never expected to explore.
Take a Closer Look at Long Lost Oakland
Explore the illustrated map and see which piece of Oakland’s history catches your eye.
How the Map Found New Life as a Puzzle
Liam hadn’t imagined Long Lost Oakland becoming a puzzle. He thought it might someday become a mural, but a jigsaw was a surprise.
By the time DeAnna reached out about adapting the artwork, Liam had spent years sharing the map through presentations, walking tours, and podcast episodes. His printed copies had run out, although people continued to ask for them. The puzzle gave the image another way to reach people, including younger audiences.
“It’s not only something that people look at now, but they really focus on,” Liam told us.
That attention feels especially suited to an image with so much to discover. While assembling a building or matching a section of the waterfront, you spend time with details that might be easy to pass over in a quick glance at a poster.
Liam has heard about the map connecting grandparents and grandchildren, and he receives photos from people celebrating their completed puzzles. The artwork can prompt someone to share a memory, ask about an unfamiliar landmark, or seek out the podcast behind it.
That connection between art, people, and place is one of the reasons this collaboration means so much to us.
Understanding What Changed, and What Continues
The title Long Lost Oakland invites us to consider what has disappeared, but Liam is careful about how those stories are told. In our conversation, he emphasized that Ohlone people remain here and that their culture continues.
The Indigenous elements pictured in the artwork belong within that ongoing history. Liam spoke about language learning, basket weaving, and efforts to return land to Indigenous stewardship as examples of people sustaining and strengthening cultural connections.
He brings a similar care to stories about other parts of Oakland’s past. The shipyards pictured along the waterfront connect to the families who came for wartime work and helped shape West Oakland’s community and culture. Buildings may disappear, but their influence can continue through people, traditions, and memories.
Liam tries to make room for loss and injustice alongside happy memories and efforts to create change. That approach gives the map depth, inviting us to think about how Oakland became the city we know and how people continue to shape its future.
Follow Your Curiosity After the Last Piece
When we asked Liam where someone should go after finishing the puzzle, his advice was to begin with whatever interested them most.
For some children, that might be the roller coaster at Idora Park. For someone else, it could be the balloon, the shipyard, or the grizzly bears. East Bay Yesterday has episodes exploring individual features of the map, so readers can follow their curiosity without starting at the beginning of a chronological history.
We like the idea of finishing a puzzle with a few new questions. Whether you’ve lived in Oakland for decades or are just getting to know it, there’s plenty in this image to spend time with, talk about, and explore.
