Is it possible to use wild cards in a URL to retrieve multiple objects located on a server, or a listing of multiple objects located on a server.
For example:
www.mywebsite.com/images/october/*.jpg
Or is there anything similar that would produce the result that I'm looking for.
It's only possible if you have a custom developed filter, handler, or application that can understand the wildcard syntax. IIS does not natively support wildcards in URLs.
It's not possible (at least in common HTTP 1.1), because the HTTP protocol doesn't work this way. For every HTTP request there is one HTTP response - the two together are called a HTTP transaction.
As workaround you could implement some sort of zip file where you collect all the files and return it as single file download.
Another approach would be a client-side (browser) implementation in JavaScript where you get the files in some sort of loop.
Both alternatives are rather theoretical solutions.