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The Roxbury Latin School (informally known as RL) is a private, college preparatory all boys day school located in West Roxbury, Boston, Massachusetts. Founded in 1645 by Puritan missionary John Eliot, Roxbury Latin bills itself as the oldest boys' school in North America and the oldest school in continuous existence in North America. Roxbury Latin enrolls about 300 boys from the seventh through twelfth grades. Its $171 million endowment (as of June 2022) allows it to admit students on a need blind basis and to provide financial aid that meets 100% of admitted students' demonstrated financial need. 38% of students are on financial aid. In addition, the school has a policy of charging frontline tuition that is "about 65% of that of other Boston area independent schools." Tuition for the 2023 24 academic year is $39,250. Sam Schaffer, the current head of the Upper School at St. Albans School in Washington, D. C., will become Roxbury Latin's 12th Head of School when Kerry Brennan retires in June 2024.

Roxbury Latin was founded by residents of Roxbury, Massachusetts to teach Latin grammar to local students. John Eliot, the local minister, believed that a religious society needed to be religiously literate—i. e., well educated. Like many of New England's oldest schools, the school started out as a one room schoolhouse in Dudley Square with a single teacher, John Eliot's brother Philip. The school's refusal to close during the American Revolution earned it the title of the oldest school in continuous existence in North America, as Boston Latin School and New York City's Collegiate School both temporarily shut down during the war. Roxbury Latin's commitment to a college preparatory education waxed and waned in its first two centuries of existence. In the 1660s it was listed as one of Harvard College's leading feeder schools, but between 1836 and 1844 the school sent only three students to any college. The instability was largely due to the school's financial model. Roxbury Latin was funded by neither taxes nor tuition fees, but by local families who agreed to pay an annual subscription in perpetuity (in reality, until 1789) for the school's maintenance in exchange for free tuition. Its budget was large enough that several distinguished gentlemen taught at Roxbury Latin early in their careers, including future Supreme Court justice William Cushing and Massachusetts governor Increase Sumner. However, for the most part, the pay was so uncompetitive relative to the tax funded schools (in some years Boston Latin paid its teachers twice as much) that most schoolmasters departed after a year or two. Roxbury Latin did not hire a second schoolmaster until 1819. The school briefly converted to a semi public institution from 1839 to 1860 in exchange for subsidies from the town of Roxbury, but was expelled from the public school system after it rejected too many students from the town's public elementary schools.

Under headmaster William Coe Collar (1867 1907), the school quadrupled in size and became the now familiar college preparatory institution. Although Collar was a classicist—he wrote popular Latin and Greek textbooks—he expanded Roxbury Latin's classical curriculum beyond Latin, Greek, and mathematics, adding courses in English, modern languages, and science. He also hired specialist teachers to cover these new subjects. When Collar retired in 1907, Harvard president Charles Eliot (no relation) said that "[t]here is no better preparatory school in the country." Many of Collar's students went on to found or lead their own schools, including St. Paul's (Samuel Drury '97), Middlesex (Frederick Winsor '88), and Cate (Curtis Cate '03). Collar financed this expansion by imposing tuition fees for the first time in Roxbury Latin's history, starting in 1882. Although these fees were high by contemporary standards—Roxbury Latin's $100/year tuition handily outpaced Andover and Exeter, and was raised to $150 in 1892—they did not raise enough money, as tuition was waived for students living in Roxbury, who at the time comprised 86% of the student body. Although Collar turned Roxbury Latin into an elite prep school, the school consistently lost money under his leadership. In the 1890s, Collar attempted to convert Roxbury Latin into a boarding school, which could charge higher fees, but the new boarding department was unpopular and quickly abandoned. The board of trustees (a majority of which, by law, lived or worked in Roxbury) repeatedly rejected any attempt to move the school from Roxbury or to impose tuition fees on Roxbury boys. These difficulties were still unresolved when Collar retired in 1907.

In the decades following Collar's retirement, several constraints on Roxbury Latin's growth were removed. In 1913, the school's charter was revised to allow alumni, and not Roxbury residents, to control the board of trustees. In 1927, the Massachusetts legislature passed an act confirming that Roxbury Latin would no longer have to educate Roxbury residents for free; however, the school did not charge residents tuition until 1935, and residents did not pay full tuition until 1961. In 1927, Roxbury Latin moved to its present location in West Roxbury. In accordance with the country day school movement, which argued that students should be educated outside the distractions and pollution of the city, Roxbury Latin's affluent alumni had demanded that the school move from Roxbury (which was now a working class neighborhood) to a more suburban location. Charles Eliot of Harvard (a harsh critic of the old board) also backed the move, writing in Roxbury Latin's promotional materials that in order to maintain the school's ability to feed students to Harvard, it was "necessary to convert the School into a country day school" by leaving urban Roxbury. The new location had a noticeable effect on Roxbury Latin's demographics. Although West Roxbury was more affluent than Roxbury, it was heavily Irish Catholic, so mid century Roxbury Latin was notably diverse (on religious grounds) by New England prep school standards. In the 1944 45 school year, Roxbury Latin educated a roughly equal number of Protestants and Catholics. In addition, Jews were 14% of the student body. In lieu of the Roxbury tuition subsidy, which for school purposes included West Roxbury, the school began offering a conventional financial aid program in 1951; by 1963 roughly one third of the student body was on scholarship. However, a proposal to admit girls was rejected in the 1970s, and Roxbury Latin remains a boys' school to this day. In 2003, Roxbury Latin hired its current head of school, Kerry Brennan, the headmaster at Manhattan's Collegiate School. Sam Schaffer, the current head of the Upper School at St. Albans School in Washington, D. C., will become Roxbury Latin's 12th head of school when Brennan retires in June 2024.

Roxbury Latin has been recognized in several lists of schools that send their students to selective universities. 2002: Worth magazine ranked RL #1 in the nation for sending students to Harvard, Yale, or Princeton. Between 1998 and 2001, 21.1% of RL graduates matriculated at one of these three schools. 2008: PrepReview. com ranked RL #1 in the nation for sending students to the Ivy League schools, MIT, and Stanford. 45% of RL graduates matriculated at one of these ten schools. 2015: MainStreet ranked RL #5 in the nation for sending students to the Ivy League schools. 36% of RL graduates matriculated at one of these eight schools. In the five year period from 2019 to 2023, Roxbury Latin placed 84 students at Ivy League schools, nearly half of whom (38) attended Harvard College. Approximately 55 boys graduate from Roxbury Latin every year.

In 2010, Forbes ranked Roxbury Latin the fifth best prep school in the United States.

Roxbury Latin has a 6:1 student teacher ratio, and the average class size is 12. The school offers Advanced Placement courses in certain subject areas, but not English or science, although students may sit for AP exams in those subjects anyway. The 54 students in the Class of 2022 took 137 AP examinations by the end of their junior year, and 74% of the papers received a 4 or a 5. 38% of the student body is on financial aid. For reference, at Roxbury Latin's athletic rival Belmont Hill, frontline tuition for the 2023 24 academic year is $61,400, a difference of $22,150. However, the average financial aid grant at Roxbury Latin is $26,258, All three schools claim to meet 100% of admitted students' demonstrated financial need.