OP. I went to Williams and while the winter is long I suppose, I grew up in New England so it wasn’t a shock for me, there is plenty to do. Firstly we (my entry) went to every home basketball game. The gym would be absolutely packed and school spirit ran high, especially for boys games. There are plenty of parties. Teams workout together at the gym off season. It’s pretty fun to be surrounded by your teammates as they cheer you on while lifting or doing a push up contest. Snow can be fun! There are tons of skiing opportunities discounted for college students in the area. Williamstown is as cute as a button. So much nicer than when I attended for sure.
I think this is a great opportunity for you, especially coming from a family that as you stated has no idea what’s going on with college admissions. You are also going to have an amazing alumni network to help you out. My husband got his very good job through an alum and he is currently creating an internship for a kid who contacted him through the alumni office.
There are plenty of kids who come from really far away and thrive at Williams. At least you have seen snow! There are going to be kids there who have literally never seen snow and never owned a winter coat or a pair of boots.
It is a scary big decision, I remember not wanting to stay when my mom dropped me off, but it was a great 4 years.