The great thing about small LAC colleges in small towns is that most of what students do is cheap or free, because it is subsidized by the college, and most of it is on-campus. Our LAC collegekid used savings from her summer job to pay for everything that wasn’t covered by room, board and books, and never needed to call home for money- yet she went to on-campus shows and concerts and competitions and all kinds of outdoor activities. There are students at all of those colleges with lots of money- and ones with none. Most are somewhere in-between.
It’s an interesting collection of places you have. I don’t know much about ConnCollege. I know a bunch of students at Colby, Bates and Wes (and I know even more about Vassar, which was mentioned upthread), and I would have no worries about being a low income student at any of them. I haven’t known any Trinity students in many years, so my perception may be out of date, but it would be the one I would look at the most carefully to see if it feels comfortable to you.