Parent of kid who only looked at east coast and midwest LACs and needed substantial (1/2 tuition) merit for us to swing being full pay – can add a few thoughts.
Denison, Wooster, Kenyon in Ohio plus Dickinson in western PA are all great ones to add to the list. Denison, Wooster and Dickinson are all a little larger, closer to 2200-2400 students, which helps with having room for kids to find their niche.
If you are willing to go further into the midwest, Earlham is a Quaker school with overlapping culture as Haverford. Kalamazoo and Knox are some of my other favorites – broad range of kids, what I refer to as the spectrum from blue hair to Vineyard Vines. We also hear great things about Centre College in KY, though never made it there to visit.
Greek life at Wooster and Knox is not traditional, drunk frat parties, (from what we hear). Denison and Dickinson and Kenyon have around 30% student participation in Greek life, and I believe all are non-residential, in that there are not separate Greek life residential facilities (though Kenyon has greek life kids clustered in the same dorm sections). From what we hear, greek life is there, but not necessary to participate in to have a social life. My kid was exploring athletic recruiting, so we attended games at all these schools – there was lots of student support at Kalamazoo, Knox and Earlham, though those campuses did not feel jocky at all – felt more like community support than sports support. Denison and Dickinson seem to us as having strong support for athletics, but also very diverse communities in terms of interests – lots of artists, social justice and other types of kids.
I agree with the comments suggesting Conn Coll might not be as good a culture fit as the summer visit suggested – my sporty/musician kid found it too split between preppy and arty, with not enough overlap between them. Keep in mind that the NESCAC schools (Bates, Conn Coll, Hamilton) as well as Haverford, Swat, will not give merit aid and I believe Haverford dropped its need-blind admissions policies, though you would want to check that. I am a BiCo community member (Bryn Mawr alum) and loved Haverford. It is a distinct community, with the importance of the Honor Code underlying the social fabric of the place.
Visiting the merit/safety schools, doing fall interviews, and applying EA to get some good admissions results with merit in hand before the end of the year is a great way to reduce stress in the fall. If your son feels that there are a couple safety/matches he would be happy attending, that takes the pressure off. Wooster has a merit predictor online, which is actually reviewed by a real Admissions person and results in a letter a few weeks later with predicted merit. My kid’s merit award at Wooster was a little higher than predicted. Kalamazoo, Knox, Earlham and Wooster all have EA, with decisions starting in late November/early December. Dickinson’s EA does not give results until Feb, which is too late to affect RD applications. Denison does not have EA, only ED 1 and 2.
Good luck, and keep up the research!