I got you if there are any questions about these schools, so feel free to ask. (I personally had to choose between them)
-Dorm Life?
-Academics?
-Sports?
-School Spirit (lots and lots)
-Dress Code?
-People?
Ask away 
Thanks for this offer! My DS is currently trying to choose between these two schools. Re “the vibe” what would you say was the major difference between the student bodies? My initial take is that Hotchkiss seemed to be a little more “sophisticated / urbane”, and less “preppy”, with a lot more kids from New York City. But maybe I read this wrong.
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Congratulations, those are great schools! First of all, I would say that the people at Hotchkiss are very refined in manner and goodhearted individuals, if that is what you meant. The dress code for both schools is fairly formal, but I agree that taft would be more “preppy.” On the other hand, the students at Hotchkiss are generally more diverse than the Taft students and the vibe here is very relaxed and positive. Nevertheless, the kids here definitely do work hard and time-management is a crucial skill that everyone inevitably learns.
Overall, both schools have amazing campuses, both are rural, but Taft is closer to a town in western Connecticut with over 20,000 people (Watertown). Hotchkiss is 2 miles away from a small town (Millerton) and kids always go over on weekends to shop, watch a movie, etc. Hotchkiss also offers a trip to Danbury Mall every few weeks or so as well.
I would say that Taft has stronger athletic, especially for boys, even though they lost Taft-Hotchkiss day this year. Taft has amazing athletic facilities, a really nice hockey rink. However, their second ice rink in the basement is horrific (they don’t show the new kids). Hotchkiss also has amazing athletics facilities, and has 2 ice rinks that are both very nice.
Hotchkiss has an incredible music and arts program as well, which definitely exceeds Taft’s arts program, but both schools do have great academic programs too. The student body of hotchkiss consists of many NYC kids, bay area, Asian, European, so lots of diversity for sure.
So yeah, if your student is more athletically focused or generally enjoys the “preppy” american feeling, Taft might be the one.
If not, come to Hotchkiss and see for yourself. (might be a bit biased, but it is true)
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