To be honest, I don't think its really something to worry about... "/Content" is going to make a pretty minimal contribution to your page size. If you still want to do it, here are some options:
Option 1, if you are running on your own server, is to check out the IIS URL Rewrite module: http://learn.iis.net/page.aspx/460/using-url-rewrite-module/
Option 2 is to use either RedirectResult, or ContentResult, to achieve the same effect in the MVC framework
First, map a "catchall" route under "Images/" to a controller action, like so
routes.MapRoute("ImageContent",
"Images/{*relativePath}",
new { controller = "Content", action = "Image" })
Make sure it is above your standard "{controller}/{action}/{id}" route. Then, in ContentController (or wherever you decide to put it):
public ActionResult Image() {
string imagePath = RouteData.Values["relativePath"]
// imagePath now contains the relative path to the image!
// i.e. http://mysite.com/Images/Foo/Bar/Baz.png => imagePath = "Foo/Bar/Baz.png"
// Either Redirect, or load the file from Content/Images/{imagePath} and transmit it
}
I did a quick test, and it seemed to work. Let me know in the comments if you have any problems!