I spent my childhood in the 5500 North section of Jefferson Park in the mid 1960's and saw (heard) the knife sharpener(there was a name my folks used for him... Tinker? Cobbler? Something...) and it truly was a neighborhood event whenever the practitioner was in the area.
Mom & Dad were protective of us kids and urged us not to hang around the cart or follow him. As I recall the operator
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