You can bulk upload files to your Documents and Media area by logging into your Website with the appropriate privileges and click the "Manage" link in the dockbar and select "Site Content" and then click on Documents and Media.
You will navigate to the folder you wish to upload the files to and then click on the "Add" button () and select "Multiple Documents".
The "Browse" link will open up a file browser on your local machine and you can then select multiple files and click "OK".
When you upload multiple files the actual file name becomes the File name and you can specify the description, tags, and permissions.
After selecting your files using the "Browse" link you will then those selected files will populate the "Add Multiple Documents" page:
They will begin to immediately upload to the folder. Once they are uploaded you can then "Save" the files with the description, tags, and permissions (must leave as guest for publicly accessible files). Once "Saved" they will be available in the folder for use.
You can then either:
• Add additional files by clicking the "Browse" link again
• Clear documents already saved
• Prior to saving, cancel the upload by not "Saving" and clicking "Back". "Back" will also bring you back into the folder structure of your Documents and Media Site Contents area.