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, vegetable-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 Oakland locals, historians, and map lovers
• Based on the popular "Long Lost Oakland" podcast series
• Highlights disappeared places, species, and features of Oakland’s past
  
• 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

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 best-selling and most meaningful pieces in the collection.

About Liam O'Donoghue and East Bay Yesterday

Liam O’Donoghue is the host and producer of East Bay Yesterday podcast and KPFA radio program. He also regularly covers the East Bay for SF Gate. His journalism has appeared in outlets such as Berkeleyside, Oaklandside, Mother Jones, Salon, East Bay Express, Snap Judgement, The Kitchen Sisters, and 99 Percent Invisible. O’Donoghue has given presentations on local history at libraries, schools and bookstores and throughout the Bay Area, as well as at institutions such as The California Historical Society, Oakland Museum of California, Berkeley City Club, and Commonwealth Club. His show has been called "The Best Podcast about the East Bay” by East Bay Express and he has been honored by Oakland Heritage Alliance with a “Partners in Preservation Award.” O’Donoghue’s quotes on Oakland-related issues have appeared in media outlets including

New York Times and Washington Post. Follow his Substack for local history news, essays, tours, upcoming events. 

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.