Free Software is software that you may use, redistribute, modify, and redistribute your modified versions. Captive software is licensed to make it illegal to do at least one of these things. I always will recommend free software over captive software.
Freeware is software you do not have to pay to use, but is otherwise in some way captive. I will generally recommend freeware over paid captive software, though you should be careful. Quite a bit of freeware (extra browser toolbars, especially) will spy on you, and freeware may have a number of other malicious functions as well.
So: here are some resources.
Datamation has a mega-list of nearly 1100 free software projects, ranging from complete operating systems to very simple text editors, which I have added to the "other links" part of the sidebar.
Nonags.com is my go-to portal for Windows freeware. All of it is certified nagware, spyware, and malware free, though I have found some pretty worthless stuff there.
Alternativeto.net provides user ratings of various alternatives to well-known software packages, and links where you can obtain them. They are perfectly willing to link to free software, freeware, and paid captive software.
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