The File import module allows you to import many files including their folder structure from the disk to Kentico CMS content repository, so that you do not have to upload the one-by-one using the user interface.
You can configure the path to your import directory at CMS Desk -> Tools -> File import.
For more details and information about File import please refer to the Module File import chapter in Kentico CMS Developer's guide.
Page url: http://devnet.kentico.com/docs/5_5r2/ecommerceguide/index.html?file_import.htm