@highschoolperson Hello, and congratulations on having some amazing options. Between Hotchkiss and Deerfield - let’s put it this way, there’s a reason for the nickname, DeerKiss.
For Music, I would give the edge to Hotchkiss - absolutely world class program. Apart from that, the schools are very similar. Size, academic rigor, faculty quality, mostly boarding, cohesive student bodies.
Deerfield has invested in some new athletic facilities, and Hotchkiss has a big budget for a new Dining Hall/revamped student activity facilities. Both schools excel in athletics, so it is sport dependent.
Reputationally - very similar. Senior student SAT scores are comparable. Historically, Hotchkiss was more academic than Deerfield in the 50s-80s, but there really is no difference now. Hotchkiss is more relaxed, Deerfield “slightly” more conservative, but really, this is superficial and relates to the dress code.
Loomis: caring administration and faculty. To be frank - downside is 30% day students, so the student body is a little less cohesive. People argue about this all the time, but we know tons of families at Loomis and they all agree about the day student/boarding distinction. Hartford is not culturally interesting, so there is no great advantage to being nearby except for Bradley airport. Probably no BS has made greater reputational strides than Loomis. I would be thrilled and honored if our youngest were accepted at Loomis.
Academically, it is slightly easier to get academic honors at Loomis than comparable honors or rank at Deerfield and Hotchkiss - just a tad.
All the best, and stay healthy and safe!