Files can be uploaded in bulk via data loader. Prep a .csv file with the local path of the files and sfdc ID of the folder in documents.
FOLDERID | NAME | CONTENTTYPE | TYPE | ISPUBLIC | BODY | DESCRIPTION
FOLDERID - The sfdc ID of the folder in documents tab
NAME - Name of the file once it's created in documents
CONTENTTYPE - The type of content like image/gif
TYPE - File type like gif, jpg, doc, pdf
ISPUBLIC - Boolean indication if the document is available publicly
BODY - The local path of the file goes here.
DESCRIPTION - Description of the document.
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