Hello woodfind,
yes, it is possible to put your picture in your TOC but I do not know how well the result would look like. You will have to play with that.
Take your picture, select it and then apply a style that you use for your Headlines (probably Heading 1). Then, when you create TOC, this picture will be included.
If you need some help on how to effectively create the table of contents, here is the link:
http://www.mswordhelp.com/2010/04/wo...oft-word-2002/
I hope it helps
Mike