Not via Hiawatha. But you can do the following trick: use the URL toolkit to redirect every request in a specific directory to a PHP script and let that PHP script use header() to set the expire flag and readfile() to output the image. Don't forget to use header("Content-Type: image/<type>") to set the correct content type of the image.
UrlToolkit {
ToolkitID = images
Match ^/images/.* Rewrite /images.php
}
VirtualHost {
...
UseToolkit = images
}
Use $_SERVER["REQUEST_URI"] in your PHP script to find out which file was requested. If a non-existing file was requested, use header("Status: 404") to generate a 404 error.