How to take files from a server using cygwin and upload them directly to a website so they can be viewed and downloaded?

Title says it all.

Basically, I have a lot of a images on a server that I have access to using Cygwin (username@ip_address). I want to know how to get all of the images that are currently just stuck on a server and take those and upload them directly to a website where they can be viewed and downloaded by anyone who has the website's URL.

I'm fairly familiar with R so that would be the preferred method, but if there are other methods, I would be more than happy to try those out as long as they work.