This is really not possible using the usual file upload field. You will need to use a Flash-based download system. Please consider something like YUI Uploader . This is a Javascript library wrapped around a special file upload system contained in a flash movie. It is remarkably easy to use. There are probably many other alternatives.
EDIT: Now there is an HTML5 function for several file upload fields. You can do it as follows:
<input type="file" multiple="true" />
Of course, this will not be well supported in all browsers. There might be a JS download library that uses HTML5 and then reverts to Flash, where HTML5 is not available. Let Google be with you :)
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