We can assign Categories to posts but not to pages.
If you have not preciously assigned Categories to your posts edit them, http://en.support.wordpress.com/posts/edit-posts-screen/ assign the Categories to theme and click “update”.
Dynamic Categories pages are automatically generated by the software when we publish posts. Next you can create a custom menu http://en.support.wordpress.com/menus/ and add the dynamic Categories pages, which are created by the software when we assign Categories to posts and publish them, http://en.support.wordpress.com/menus/#adding-category-pages then you must clearly undertsand that dynamic Categories pages are not the static pages that bloggers create.
Here’s a link to a custom menu walkthrough > http://onecoolsitebloggingtips.com/2011/08/11/wordpress-com-custom-menu-walk-through/
There are many common errors, misunderstanding and misconceptions when creating custom menus and you can read about them here > http://wpbtips.wordpress.com/2011/12/19/custom-menus/
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