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Tourists from [Massachusetts] to Portland Maine are often faced with the maze of one-way roads on non-parallel roadways. As the end destination is usually the Promenade at the top of the hill, many a Masshole has given up in frustration and driven up the hill [going the wrong way] on one of the smaller [residential] roads. The trepidation seen in these cars mimics an adventurer reaching a summit. The nickname resulted.
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