Long Lost Oakland Puzzle, a 500-Piece Illustrated History by T.L. Simons & East Bay Yesterday

Puzzle Details

• 500 pieces
• Finished size: 16” x 20”
• Includes a printed reference image
• Features hand-drawn illustrations of disappeared places, animals, and landmarks in Oakland

Eco-Friendly Packaging

• Printed on 100% recycled ESKA chipboard
• Uses non-toxic, soy-based inks
• Puzzle pieces are stored in a reusable, resealable bag
• Packaged in a giftable, sustainably sourced box
• Manufactured using socially responsible production practices
• Learn more about our Sustainable Manufacturing Practices

Why You’ll Love It

• Sales directly benefit East Bay Yesterday
• A perfect gift for East Bay locals, historians, and map lovers
• Based on the popular "Long Lost Oakland" podcast series and walking tour
• Highlights disappeared places, species, and features of Oakland’s past
• Combines local storytelling, activism, and hand-drawn art
• Created by independent media and small business collaborators
• Puzzle is frame-worthy, educational, and screen-free
• Supports local storytelling through East Bay Yesterday

About the Puzzle

Making a puzzle out of this image was one of our inspirations to start Oakland Puzzle Company.

The Long Lost Oakland Puzzle is more than just a puzzle. It’s a tribute to the forgotten geography and memory of a constantly evolving city. 

This 500-piece jigsaw is adapted from a hand-illustrated map created by T.L. Simons in collaboration with the popular independent podcast East Bay Yesterday.

Featuring animals, buildings, plants, and landmarks that once existed in Oakland but no longer remain, the map explores themes of displacement, transformation, and memory. From vanished creeks to demolished structures and lost species, each detail invites puzzlers to consider the layered history beneath Oakland's streets.

This collaboration was one of the original inspirations to launch Oakland Puzzle Co., and it remains one of the most meaningful pieces in the collection.

About East Bay Yesterday

East Bay Yesterday is a critically acclaimed podcast produced and hosted by Liam O’Donoghue. Since 2016, the show has explored the history, culture, politics, and nature of Oakland, Berkeley, and the greater East Bay. Named “Best Podcast About the East Bay” by East Bay Express in 2017, the show also airs weekly on KPFA 94.1 FM.

Learn more at eastbayyesterday.com

About the Artist: T.L. Simons

T.L. Simons is a graphic artist and game designer based in Philadelphia, formerly rooted in Oakland and Berkeley. His work spans illustration, community publishing, and politically engaged design. He was a collective member at Inkworks Press, a hub for radical printing in Berkeley, and later became a well-known figure in the Oakland design community.

T.L. is also the creator of Outlandish Games, and his work can be found in books, zines, games, and maps across the country.