1847, "rough, heavy kind of shoe," later "long, cheap cigar" (1873), both shortened from Conestoga, rural region near Lancaster, Pennsylvania; both items so-called because favored by drivers of the Conestoga style of covered wagons first made there.
n. a cigar. : Then this guy pulls out a big stogie and starts to smoke it right there in the restaurant.
Dictionary of American Slang and Colloquial Expressions by Richard A. Spears.Fourth Edition. Copyright 2007. Published by McGraw Hill.
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Example sentences from the web
The cheroot or stogie is a cylindrical cigar with both ends clipped during manufacture.