The school was initially headquartered in Pelham Manor, New York, but moved to Watertown, Connecticut in 1893.

[3] However, Horace Taft came from a famous Ohio political family, and the school developed a reputation for preparing children of the Midwestern gentry for Yale's entrance examinations.

[5] In 2015, Business Insider ranked Taft the 14th-most 'elite' boarding school in the US, based on a formula that equally weighted financial endowment, average SAT scores, and acceptance rate.

[1][7] In 2018, Architectural Digest named Taft the most beautiful private high school campus in Connecticut.

[12] The school's athletic facilities include an 18-hole golf course, 16 tennis courts (four indoor), eight squash courts, two field houses, two tracks (one indoor, one outdoor), two ice hockey rinks (one Olympic-sized and one NHL-sized), and more than 10 playing fields.

[13][14] Taft and its athletic rival Hotchkiss compete in the Founders League, a group of prep schools mostly located in Connecticut.