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7/18/06 11:15 pm (UTC)
Not wikipedia, as it turns out, but google:

The phrase in question here, of course, is riding the rail or to be run out of town on a rail. You may be surprised to learn that it has nothing to do with the railroad and everything to do with with a fence rail. How does one ride a rail? This is a form of punishment in which a person is tied or held to a rail that is then paraded through town, and often out of town, on the shoulders of two or more men, presumably strong men. The object is for all to see the transgressor and immediately recognize that he has done something wrong by virtue of the fact that he is tied to and riding on a rail, and thus to humiliate him. The OED dates the phrase to 1834, but it was clearly a familiar expression even then and so was certainly around prior to that. Knowing this, we did some of our own research and found the phrase in the Edinburgh Advertiser of August 23, 1776! Here is the excerpt we found:

Extract of a letter from a gentleman at Sandyhook dated July 6, 1776.
"The poor Tories, as the King's loyal subjects are called in New York, are suffering the most cruel persecutions; some have been obliged to ride skimmington on a rail, till they died; one was lately executed; others are confined in gaol in irons."

If you're wondering, skimmington is defined by the OED as "a ludicrous procession, formerly common in villages and country districts, usually intended to bring odium upon a woman or her husband in cases where the one was unfaithful to, or ill-treated, the other. Also attributive." The phrase ride the Skimmington ("hold a Skimmington procession") also turns up in the written record in 1697, but our find is a bit different in that Skimmington is being ridden on a rail. If you're wondering where Skimmington came from, it is thought to come from the notion of a wife beating her husband with a skimming-ladle, with the addition of -ton (as in simpleton). It dates from 1609.

Today it is amazing how many references one can find on Google to riding a rail meaning "taking a trip on a train". It appears that the "punishment" sense was lost and the phrase was re-adopted with what folks today would consider a more literal meaning.

(from "Words to the Wise: Your etymological questions answered" here: http://www.takeourword.com/current/page2.html)
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