Well there are several ways to update your FreeBSD machine, one of them is to CVSUP, or you could reload the machine from scratch, reloading from scratch is a pain, due to you loose any and all settings your might have placed onto your box.
I am going to walk you through a very easy way to completely update your box with the newest ports collection.
You will need the following file ports-supfile , with this file, you need to have installed the CVSUP listed already in your ports collection. Once you have the CVSUP installed on your machine, type the following. cvsup - ports-supfile need to type this where you have placed the ports-supfile. Once it does this, you will get a screen up, click on start, and it will start updating your ports collection.
That Is all there is to it, once its done, you don't have to reboot, just exit the program, and your ports collection is now updated.