Starting with the caveat that things have probably changed since my day . . . if your DS has a "weekend" (meaning he's a youngster or more senior), I THINK he can go as far as he's comfortable with. In my day, you didn't have to fill out a leave chit for WEs but you did have to sign up and provide an address and phone number where you could be contacted. People took WEs after football games in NY and Philly.
If I were you or your DS, I wouldn't pick anyplace that is more than a couple of hours away (car or train). It's not the time to fly anywhere (even if you're technically allowed to) -- save that for Thanksgiving. Unlike leave, USNA is much less forgiving if you show up late on your return, which is a distinct possibility if you travel far.
My parents lived about 50 miles away and I typically went home on long WEs. If you live further away and want to see your DS, I suggest YOU fly or drive to Annapolis or the vicinity (i.e., Baltimore, Washington, DC, etc.).
