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New York Mayor McClellan
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1918 Ford
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1908 crippled childrens outing, click on this (well, all of them) to get full size, and check out the one woman in the backseat of each car... they are all wearing a bee net over their hats. Fashion of the time, but what a goofy look.
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1903 Winton
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1917 Moonlight joyride... how far out is that, on the tractor adapter.
1910 Stanley Steamer
1913 Insurance patrol
Images via http://www.shorpy.com/