The instructions for uploading an image and linking it to an external URL are found in this support documentation entry http://en.support.wordpress.com/images/
Once you have uploaded the image and linked the URL to it in a draft post you can switch the editor form “Visual” to “HTML” and copy the code. Then you can open a new tab and go here > Appearance > Widgets
Locate a “Text” widget and then drag and drop it into the “Sidebar” box. Click it to open it and paste the HTML code for the linked image into the text widget. Then click “Save” and “Close”.
The image widget would be useful for that. You can use a link to an image from another site or from your an image you have uploaded to your WordPress.com blog media library.
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