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I've always been fascinated by these two words, as they seem to have the exact opposite meaning as expected. Is it because of the etymology? Or perhaps the meanings were switched at some point in time?

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Excellent question and a fun thing to confuse people who are new to English with. –  Darryl Hein Feb 13 '11 at 3:06
Wonderful question –  Arjun J Rao Feb 13 '11 at 4:42
I, for one, am always sober on a highway –  Dancrumb Feb 23 '11 at 1:35
Give points to George Carlin for the question. –  Bruce James Mar 11 '13 at 18:05
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1 Answer

up vote 20 down vote accepted

A parkway is supposed to be a pleasant scenic place, like a park.

A driveway is probably the only place on your personal property that you can actually drive.

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A place you "drive into", per se. –  Justin L. Feb 13 '11 at 4:48
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