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These signs have been produced from the 1930s onwards, or were at least most active in the 30s. Seen throughout the state of New York. There are two faces present. The larger one being a bit more unusual than the smaller face – note the somewhat odd shape of the 'O' and the 'U' in 'Hudson'. News Gothic seems like a close but not perfect match for the smaller face – but that's as close as I'm getting to figuring it out.