Here's one approach.
OF COURSE, ALWAYS START BY MAKING SURE YOU HAVE A BACKUP OF YOUR TW FILE!!
Using an advanced text editor like Emacs, get a list of your images and put it into a format like this:
CIMG2199.JPG: x
CIMG2200.JPG: x
CIMG2201.JPG: x
CIMG2202.JPG: x
Paste this into a tiddler called "MyImages" and change the type to data dictionary. Save the tiddler.
Create another tiddler with the following contents:
\define gluepath() $(path)$$(image)$
<$set name="path" value="file:///D:\data\graphics\file-us\">
<$button>Make Image Tiddlers
<$list filter="[[MyImages]indexes[]]" variable="image">
<$action-createtiddler $basetitle=<<image>> _canonical_uri=<<gluepath>> type="image/jpeg">
</$list>
</$button>
</$set>
Change the "path" variable to whatever address is needed for image directory and system (I used file:/// but you don't need that for images positioned relative to your system).
Click on the "Make Image Tiddlers" button, and a "Image Tiddler" (_canonical_uri based) will be made for each image.
You can of course play with this to use other image dictionaries, paths, etc. A similar technque could be used to generate image wikitext if you don't like Image Tiddlers. Note that if you are on windows that you can't use drive names like C: in the data dictionary (that's why I applied the path outside the dictionary).
HTH
-- Mark