n.b. Please drop the "\r". You should never hardcode a CR into plain text, in Perl. Let the automatic conversion from "\n" to CRLF, when printing to a filehandle without binmode applied, on a platform that wants the CRs, take care of that. "\n" is the logical end-of-line character, on any platform.

But, that aside, even though you're well on the way, your program has a bug. It will try to add a linebreak in the last line, even if it's narrow enough to fit onto one line. Why would it do that? Because

$_ = "Hello, world!";
/.{0,76}\s/;
[download]

matches the space between "Hello," and "world!".

I'd change the regexp to the following:

s/[^\n\S]*(.{1,76})(?:\s|$)/$1\n/g;
[download]

with the following rationale:

• It'll match as many characters up to 76, until the end of the string (!) or to the last whitespace character in that substring, whichever is longer
• /./ doesn't match newlines, thus it'll leave embedded short lines (ending with a "\n") unchanged, and try to match again, directly after the following newline.
• You likely don't want leading whitespace after a wrapped line — though you probably will want to keep embedded empty lines.
• You're not interested in autogenerated empty lines, hence the requirement for at least one character. /.{0,76}(\s|$)/g tends to match twice at the end of the string: first with a non-empty string, till the end, and then again with an empty string. BTW IMHO this is a bug — I don't think anybody actually wants this behaviour.

But, I admit: mine doesn't quite look as easy as yours, any more. :)

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