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Either "wɪnd" or "waɪnd" is acceptable, according to Dictionary.com, but merely being acceptable doesn't satisfy me. "Wɪnd" seems better to me, due to the connotation of blowing wind, etc, but apparently "waɪnd" is preferred, being listed first. Which was originally intended? (Or does it really not matter?)

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Could you please provide a link for your reference at Dictionary.com? Whynd draws a blank for me. – Firstrock Aug 30 '11 at 2:48
@Firstrock He meant the pronunciation, not a word. – simchona♦ Aug 30 '11 at 2:50
@Firstrock: Hopefully it makes more sense now. I was up too late last night and didn't have time to follow up too closely till this morning. – Daniel δ Aug 30 '11 at 12:01
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So are you asking which pronunciation was first etymologically? – Peter Shor Aug 30 '11 at 15:46

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According to the Oxford English Dictionary, the pronunciations /waind/ and /wihnd/ are used to indicate different verbs. They write:

Etymology: < wind n.1 In ordinary prose use the pronunciation is /wɪnd/ except in sense 3, where it is /waɪnd/

The sense 3 that they give is:

trans. To sound by forcing the breath through, to blow (a wind-instrument, esp. a horn).

So the wind in respects to a horn would be waɪnd.

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But Dictionary.com allows either. I suppose it's just being lenient. – Daniel δ Aug 30 '11 at 12:00
Merriam-Webster online also says that both pronunciations are allowed for the meaning of blowing a horn, as well as both past tenses winded and wound. They don't say whether both pronunciations of the vowel in winded are allowed, but the OED says the preferred past tense is winded, pronounced /waɪndəd/, although wound is also acceptable. – Peter Shor Aug 30 '11 at 19:57
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If your question is: was wind (blow a musical instrument) originally pronounced like wind (wind up a clock) or wind (as in wind and rain), I believe the answer is both. Merriam-Webster dates this usage to 1586, shortly before Shakespeare started writing plays. William Shakespeare repeatedly rhymed wind (as in wind and rain) with find and kind, which I assume would also rhyme with wind (wind up a clock), as they do today.

Nor can I fortune to brief minutes tell,
Pointing to each his thunder, rain and wind,
Or say with princes if it shall go well,
By oft predict that I in heaven find:

The pronunciation has changed since, so the sonnet no longer rhymes.

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Ah, so "wind" (that blows) was originally pronounced waɪnd. That explains why "winding" a horn is pronounced that way, but not why "wind" (that blows) changed pronunciation while "winding" a horn didn't change. – Daniel δ Aug 30 '11 at 19:23
Well, inertia might have tended to keep the long i in "wind" (blowing a horn), if people perceived these as different words. The real question is why "wind" (that blows) changed pronunciation. – Peter Shor Aug 30 '11 at 19:45
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When did the pronunciation change? I strongly suspect that it changed quite a while before people started using wound as the past tense of wind (to blow); for these people, the use of winded or wound was probably determined solely by the pronunciation of wind. Using Google books, I found a use of wound (a horn) in 1805, and several uses in the immediately following years. So the pronunciation of wind (that blows) changed somewhere between 1600 and 1800. That's still a big gap. – Peter Shor Aug 31 '11 at 22:44

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