Rob Garross moved from his home in Waukegan, Illinois, to Berkeley in 1980. He bought his house on Fifth Street in 1996.
Walking his neighborhood, Garross was inspired by an old wooden caboose on a nearby railroad siding. In the 1980s, advances in railroad technology such as flashing rear-end devices, and end-of-train devices, intersected with corporate goals of reducing labor costs to spell the end of the caboose. They were sitting around, there for the buying.
When he was 25, Garross rode a caboose from Great Falls, Montana, to Everett, Washington. As was fitting for a young man of his generation, he had been inspired by Jack Kerouac’s On the Road.
In 1998, he decided to buy a caboose to put in his driveway, but there was no internet for caboose shopping, so he visited railroad yards, first in Barstow and then in Sacramento, where he found and bought a late-model Southern Pacific bay window caboose.
He laid railroad track down the middle of his driveway and had the caboose trucked to Berkeley from Sacramento, then had a crane lift the caboose off the truck and into place
http://quirkyberkeley.com/trains/
https://www.berkeleyside.com/2015/09/14/how-quirky-is-berkeley-a-caboose-on-fifth-street
For the flip side, over at https://www.thecrucible.org/caboose/ they found a 1941 caboose in a backyard that they could have for free if they would remove it, fix it up, and use it as an office
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