Huddleston obtained books and funding for the school from the Society for the Propagation of the Gospel in London.

The first Trinity students, boys and girls, in addition to religious instruction, also learned to write plainly and legibly and were taught enough arithmetic to prepare them for employment.

These eighteenth-century Trinity students were almost invariably apprenticed to trades such as blacksmith, bookbinder, carpenter, cordwainer, mason, mariner, shoe binder, and tailor.

In 1895, Trinity moved to its current location at 91st Street between Amsterdam and Columbus Avenues in the Upper West Side of Manhattan.

[6] In 2004, The Wall Street Journal ranked Trinity as third best at getting its students accepted to some of the country's most exclusive colleges.

[9][10][11][12] The Lower and Middle School courseloads are highly structured, and ninth and tenth graders are offered limited flexibility in their courses.

[15] The school also has dynamic dramatic art showings with performances ranging from plays to musicals, both as classes and as extra-curricular events.

A yearly Shakespeare play is student-directed by The Nicholas J.P. Kau '08 Shakespeare Appreciation Society[16][17] Previous plays have included Julius Caesar (2017), Much Ado About Nothing (2018), Romeo & Juliet (2019), A Midsummer Night's Dream (2020), Twelfth Night (2021), Comedy of Errors (2022), The Taming of the Shrew (2023), and Macbeth (2024).