My friends and I go to Okemo pretty frequently; It's where I learned to board. I would say overall that this is a great learning mountain where you can gradually increase your difficulty level while still having fun. There are some pretty good fast and steep runs, but it's just not a huge mountain. I would say that this place is great for large groups of friends because you can easily meet up if you're separated. The town of Ludlow is super cool, with a lot of good restaurants. Also, there's always ski houses available for rent in the surrounding area which are pretty cheap. The proximity to my home-base of NJ is great too as it's typically a 6 hour drive up on a Thursday night. If you are lucky enough to get some fresh snow, it's an awesome time.
Watch out for icy patches, if you hit an icy patch, you're gonna fall and you're not gonna have a good time.