Berkshire, their aviation program looks very cool.
SMS or Loomis?
Loomis! The campus is stunning and I love creative writing.
Groton or Deerfield?
Groton! I had a great tour there, and I like their Classics department.
Blair or Peddie? (I don’t know if this one has been done before, I’m sorry if it has!)
Blair!
Exeter or Hotchkiss?
Hotchkiss! Beautiful campus and everyone was so nice when I visited! (I didn’t visit Exeter).
Andover or Choate?
definitely Choate
Horace Mann or Trinity
I have no idea so I’m just gonna say Horace Mann 
Berkshire or Kent?
Maybe Berkshire? I’m not sure. I visited Kent and it felt preppy to me but I might be wrong, their engineering was really good and have three robotics team though.
Hill or SMS?
SMS!!!
St. Paul’s or NMH?
NMH. They make their own ice cream, as I’ve mentioned numerous times.
Millbrook or Milton?
I do like ice cream!
I’d go with Millbrook. The campus is big and they have their own zoo!
Canterbury or Groton?
Groton. In spite of, not because of its selectivity. (Did you know it is tied with Thacher for most selective? Only 11-12 percent of applicants are admitted!).
http://www.businessinsider.com/most-selective-boarding-schools-in-america-2016-2
Middlesex or St. Mark’s? Don’t forget to explain why!
Middlesex because they have more students and i think a larger campus. Also, St. Mark’s has Saturday classes, and all classes everyday instead of that thing with two times a week.
Thacher or Pomfret?
Thacher, Thacher, Thacher. Friendliest, happiest campus we saw. Though if you’re into partying with alcohol or drugs, you might want to pick a different boarding school.
George School or Westtown?
George School, more people in the upper school cuz Westtown is k-12.
Suffield or SMS?
Definitely SMS. I never visited SMS but did visit Suffield a few times for basketball games and didn’t have a good experience. No offense though, it might be just not for me.
Madeira or Hun? (if anyone knows anything about them)
Madeira! While I’m unable to attend lol it’s a wonderful school
Salisbury or Avon?
Avon (if I was a guy) because I hear about it more
Groton or St. Paul’s?
St Pauls
Deerfield or Hotchkiss? Why?