Vassar and Williams are the two colleges I know the most about!!! I have had family members at both, and they’ve loved them both!
I would say your son can find his type of people at both. Both attract super-smart kids, and among the super-smart, there are often the quirky. Many types of students exist at both colleges.
I remember the first time we visited my son at Williams. My spouse and I were eating by ourselves in the dining hall and walking around campus on our own while our son was off doing some event. We commented to each other that the most prevalent type appeared to be neither jocks nor preppies, but rather nerds! It is a comfortable place for smart, quirky kids. And so is Vassar.
The other good thing about both of those colleges, compared to some others, is that there is a built-in social group for freshmen, which helps with meeting people (especially helpful for the slightly awkward or introverted among us). At Vassar, you are assigned to a house where you will live for your first three years. That helps build a lasting community. At Williams, you are assigned to an “entry” (dorm group) of about forty freshmen and 3-4 unpaid Junior Advisors who are like big siblings, as well as being part of an EphVenture group during orientation.
If you visit Williams, walk down Spring Street and you will see a store that might interest your son. It has board and role-play games and people can come by and play them. Some games are set up on tables and clearly in progress.
College isn’t always easy socially and there may be ups and downs and lonely moments. For anyone. It’s an adjustment. But I agree that colleges like these two, which emphasize community, can be helpful during this adjustment.
Which “feels” better to your son? He should pick that one. They’re both great.