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Probably all decent browsers prevent arbitrary filesystem access. You can however use javascript to select all files in a directory and iterate over them creating an upload field in your multipart form for each one of them.
There are some freebies out there, e.g. http://blueimp.github.com/jQuery-File-Upload/
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It sounds like your are looking for https://github.com/tstone/django-uploadify. If you need some more details, also have a look here: Uploading multiple files in Django through one form field.
And just saw, that blueimp comes with builtin Django Backend as well
However, be aware, that you need “modern” browsers for this to work :-), it will probably not be compatible down to IE 6 or 7
Source:stackexchange.com