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Stop 3 of 16

Key Route Inn

headphones 02:06

To spot the former site of the Key Route Inn, look for where a grand, castle-like timbered building once stood, complete with an archway big enough for a streetcar to roll straight through its heart-imagine a giant old English manor, right along what’s now West Grand Avenue.

Alright, imagine you’re standing right where, over a century ago, one of Oakland’s most impressive hotels proudly stretched across the street, its mighty wooden beams and open timbering promising comfort and adventure. It was the Key Route Inn, a place that looked straight out of an English fairy tale-turrets, pointed gables, and even a giant American flag waving atop its central tower. But this wasn’t just for show: this hotel pulled off a magic trick you wouldn’t see anywhere else in the Bay Area! In the middle of its grand archway, streetcars from the Key Route zipped directly through, dropping off travelers into the lobby itself. Picture the rattle and clang of wheels and the buzz of guests arriving, all echoing beneath the hotel’s wooden rafters.

This place overflowed with energy. Presidents-like William Howard Taft and his whole entourage-stayed here, maybe hoping the beds were as solid as the oak beams. Some say guests rushed their bags inside, eager to catch the next streetcar tram or just gawk at commuters chugging through the lobby. The whole building seemed almost alive, a crossroads for travelers, dreamers, and a few lucky bellhops.

But fate, as it often does, had other plans. In 1930, a massive fire licked at the old timbers, and much of the magic began to fade. The city was changing fast, too, and soon, progress called for roads where once stood railway arches and chattering guests. Demolition crews moved in, and by the spring of 1932, the grand Key Route Inn was gone-just 25 years after its dramatic debut. Still, close your eyes and listen carefully; perhaps you’ll hear the faint whistle of a streetcar or the distant laughter from a bustling lobby, as if the past just doesn’t want to let go.

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