I went for the first week in 2002 (10U). It is, quite honestly, the best baseball trip I've ever taken. You are treated well, and the baseball is top notch. The scenery is wonderful and the friends you make will last a lifetime. Cooperstown itself is pretty much what you'd expect - a very quaint little town with lots of hospitality.
Part of the umpire program is that you get a ticket to the HOF. I spent 5 hours there and I think I read every plaque. It was almost a religious experience for me and the completion of a dream I've had for a long time.
Basically, here's how it goes. Check in on Saturday and start calling games on Sunday. We only had 30 or so umpires that week, so I did about 5-6 games a day and a semi-final on Thursday. Now, there's so many that go (up to 60 a week) that I'm sure the most you'll do is 2 or 3 a day, so you'll have plenty of time to look around.
I think the best part is that there are 14 fields with NO stands from first around to third. Just a big, green wall, like a Fenway. All the parents sit in a area down the 1st and 3rd base lines, so the kids just get to play without any 'interference'.
They feed you, although the diner down the street is a great alternative.
If you need anymore info, just e-mail me.
BTW, go to the website and click on the week of June 14, 2002. I'm the tallest guy in the back of the umpire's picture.
"Also, did your family go with you?" No. There's no accomodation for them on the site. They'd have to stay at one of the few hotels in town. Besides, go there once and enjoy it. Then, later on, go back and share with your family.