Upgrading from CS3 to CC. Should I upgrade to CS5 or CS6 first to be sure my older files will still function?

I want to upgrade, but I want to do it smart so my files will all still open and work.  Now at CS3, do I need upgrade to say, CS5 or CS6, before going to CC?

No need for that. Older files will always open.
(The other way around can sometimes be more difficult, in case of new features that weren't there in the old PS version. But that too usually works with the "maximize compatibility" option checked).

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