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Is it an old farming metaphor, or a military saying? Where did this(these) saying(s) originate?

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Is this a possible candidate for the eggcorn tag? – zpletan Mar 27 '12 at 18:48
@zpletan Thanks. – Major Stackings Mar 27 '12 at 18:52
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This is in the eggcorn database, unfortunately no genealogy is given. – Mark Beadles Mar 27 '12 at 19:05

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up vote 12 down vote accepted

The original form of the phrase appears to be "a hard row to hoe". Now, "tough row to hoe" is found at least as far back as 1890:

She's got a tough row to hoe, Dilly Gage has. She used to try to keep folks from knowin' how cantankerous he was, but she couldn't.

while 1963 seems to be the earliest occurrence of "tough road to hold", and it is noted as an error:

Certain little errors may be the result of spelling, hearing, or carelessness - "a tough road to hold"

But we find "hard row to hoe" even earlier. It's found in Dickens' All the Year Round magazine in 1890, but the earliest use is no later than 1818:

He loves to contend with difficulties; and if he had not a hard row to hoe, would place himself in some sphere demanding effort, in order to extricate himself.

Since it's used without explanation in the 1818 book, it must have been regarded as a well-known expression even by then. So the origin is as a farming metaphor, and seems to be chiefly American in usage.

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There is a supposed 1800 reference in that Google search, but it is wrong. Google indexed the year that work incorrectly. It is not from 1800, but from 1899, as you can see in the title page and headers of the work itself. – Mark Beadles Mar 27 '12 at 19:38
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haha - I saw your comment as soon as I hit Post your answer. You're quite right, of course. So I just went back and changed mine to the next oldest citation, in 1818. I doubt the road/hold variants would have turned up until much later, but to be honest I can't be bothered to check that myself just now. – FumbleFingers Mar 27 '12 at 19:48
up vote 2 down vote

The road and hold variants are eggcorns deriving from the orginal "Tough/hard row to hoe", an agricultural expression relating to hoeing one’s row (with an actual tool) while working in the field, that goes back to at least 1818.

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