That is why I added the caveat that I did.
Purely anecdotal, but in my circles kids would often start off considering Dartmouth alongside various LACs, and then after visiting some would make it a top choice, and others would strike it from their lists. Polarizing is probably the wrong term, but it does seem to draw strong reactions both ways on a visit.
Unlikely to be idiosyncratic to Dartmouth, of course.
Small sample but I have known 3 Midd graduates, 2 loved it, one was miserable there and says her biggest regret is that she didn’t transfer out. But as OP has a sibling there I would assume they are at least somewhat familiar with the campus and the culture.
I think it’s worth keeping in mind– both for the OP as well as anyone else- that a LOT of colleges are ‘fit schools”. Either because of their mission (BYU, Liberty, Oral Roberts) or their location (BU/NYU/GW vs. Dartmouth, Hamilton, Williams) or their academic focus (CalTech, RPI, Embry Riddle). And then there are colleges which, for the most part, have something for everyone- Michigan, UMD, Wisconsin. Although a PARTICULAR kid might be unhappy at the “something for everyone” schools, most kids find their tribe, figure out the upsides and downsides of the geography and weather and location, and figure out a satisfying course of study. When folks post here that Wellesley is “too remote” (Wellesley is in a gorgeous and upscale suburb of Boston with both public transportation to the core of downtown Boston as well as frequent shuttle buses to Cambridge) or that Northwestern is “too urban”, it helps to ask what the person is comparing it to in order to be helpful. Wellesley is not urban like Northeastern but is hardly remote; Northwestern isn’t bucolic like Williams but is NOT in the urban core of Chicago– etc.
My kid goes to Pomona (just finished her sophomore year) but was accepted at Dartmouth and attended an overnight admitted student day there. We also toured it a few years ago. She chose Pomona because of its location (we’re on the West Coast but not California) and program (studio art), but the financial aid was better at Pomona too. I don’t know much about Midd, but it sounds cool. I also know nothing about urban planning or how it fits into the curriculum of any of these schools.
My advice is to not apply ED unless you are super confident in your choice. It offers little advantage at either Pomona or Dartmouth. It’d be much better to make a decision next spring after having the opportunity to visit both schools. Also, what you want in a college may change a lot in the next nine months or so.
Anyhow, I really like both schools. I feel like Dartmouth kind of gets a bad rap on this forum because of what it was (or was people thought it was) in the 80’s and 90’s. You may not like the Greek system, but my impression is that it’s very different than it was in the past. I live in the mountains and I really liked its location and proximity to outdoorsy stuff. It seems very social. I have a half dozen or so friends who went there, and all of them seemed to have enjoyed their experiences. Also, all of them are much further on the nerd end of the nerd-bro spectrum. Honestly, Dartmouth seems to be a great school and a great experience.
Pomona and the 5Cs are great, but certainly not perfect. IMO, Pomona took most of the good things about schools like Williams, Amherst, Bowdoin, and Swarthmore while avoiding some of the bad things (historical exclusionary practices, legacy admissions, heavy athlete percentages, etc.). It has a reputation for being more laidback, and while I can’t prove that it is, the culture is the opposite of cut throat. It seems like kids are extremely social in terms of doing thing, but it’s a pretty terrible party school. The better parties are at CMC and Mudd, and even still the 5Cs together are not particularly known for any party culture. The 5C Consortium is truly fantastic and probably represents Pomona’s standout feature. The schools are very integrated socially and academically. I really like what each school offers and brings to the Consortium generally.
Pomona is excellent for the outdoors with the caveat that you need to use a car. But in my humble opinion as an outdoors lover myself, the opportunities blow the doors of anything in New England. My daughter goes hiking on Baldy quite often, seems to make a couple beach trips each semester, has stayed in a cabin near Mammoth, has made trips to Zion and Escalante, and did a backpacking trip in Big Sur. She also seems to visit Los Angeles a few times each semester. That said, if you want to do casual hikes straight from campus, Dartmouth or Midd are probably better. But if you want to experience the outdoors on a grander scale, I’d much prefer Pomona. YMMV.
Pomona is extremely liberal. I think the students are certainly tolerant, but I don’t think you’re going to get a lot of political discussion in which all sides are represented.
We’re not Jewish, but I think you’ll certainly find many Jewish students at Pomona and the 5Cs. There was recently quite a kerfuffle on campus about Palestine/Israel, with the former seeing more support than the latter, if that matters to you. Los Angeles also has one of the largest Jewish populations in the world.
I’m from California, went to UCLA, and I don’t see any credence to the fakeness notion. I’m guessing that perception comes from Hollywood. If you work and mingle in that particular business, you’ll probably see a bit of superficiality. But you shouldn’t see much of it elsewhere, particularly in Claremont. Also, Pomona traditionally has the lowest percentage of Californians of any college or university in California. Again, the vibe of Pomona seems to be intellectual and humble. The kids who go to Pomona are going to be very similar to those who to Bowdoin, Swarthmore, Williams, etc.
By the way, maybe you should check out Bowdoin? It seems to check many of your boxes. I thought it was a very cool school, and like Pomona, seems to have a reputation for being a little more laidback than some of its peers.