I'm by no means an expert at all, but the front truck with the tires in the bed looks like a fourth generation Ford F100, they were made between 1960-1966. A couple cars down from the Ford, there's a blue and white truck that appears to be a newer Dodge D100 Sweptline pickup, I'm guessing it's a 1963 or 1964 model. There's also a black with white striped Chevy Sidestep pickup and it also looks brand new, I'm guessing that one is a 1964 or 65. It's hard to say because of how far away they are. Great picture though!
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The latest I can positively ID is the white 1962 Chevy two door sedan 8th from the left in the line of cars parked perpendicular to the concrete wall. Although the black Chevy pickup on the far right might be a 1963. ( I had an AMT model of this pickup.)
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Ted - I would try to contact Tom Farence in the list of contributing photographers to this site. Tom is an ex-Milwaukee train driver. Maybe he can give you more clues.
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The Fourth Gen truck you believe to be a Ford is actually an International. To the left of the black Chevy PU on far right, is a Black 65 or 66 Chevy wagon. Left of that a 64 Tempest / Lemans and above it a Burgundy 66 Chevy wagon. Clarity a bit off in this vintage shot, but what a collection of classic cars and locomotives !
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