I agree with @blossom about Middlebury being more outdoorsy. If he likes to hike, camp, and ski, he’d fit in no matter where he went to high school. Same with Williams, Bates, and Bowdoin, IMO. They, along with Haverford, all have pretty similar numbers of participation in sports, but it’s more of a my-roommate-is-on-the-track-team vibe than tailgating/football.
Vassar a little less sporty since they don’t have a football team at all. The others listed do (I think.) Football has a huge roster. And then to comply with Title 9, a school would need to have an equal-ish number of women in sports. I’m going to guess that the biggest roster at Vassar Men’s Athletics is probably track. So, again, different vibe.
Actually this website might be helpful when it comes to figuring out what %age of students are in varsity sports: https://ope.ed.gov/athletics/#/
Wes is easy to fly in and out of Hartford CT.