Is there a way of updating blender with all of my files contained? I want to update blender to the latest version, 2.77, I'm currently using 2.75, and I know you can update blender by reinstalling the program, but my only concern is that would my files be imported into the next version. 

And if not, how would I do so?
Your .blend files will still be accessible. Blender is backwards compatible way past 2.75.