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.
"Don't take that road, I saw someone turn onto it from the other end. Though you can if you wanna watch another one complete the Masshole Summit."
by justsomerandomdude123585346 July 11, 2018