Дариенская старшая школа: достижения и развитие

Darien High School was specifically ranked 22nd in the nation for best STEM high school by U. S. News & World Report, a list of the top science, technology, engineering and math schools in the United States. Of the 200 graduating seniors in June 2017, 13 won national recognition in the National Merit Scholarship Program, with 13 as "merit finalists" and three as National Merit Scholars. For the purpose of comparison with the achievement levels of similar schools, the state Department of Education classifies schools and communities in "District Reference Groups," defined as "districts whose students' families are similar in education, income, occupation and need, and that have roughly similar enrollment." Darien is one of eight school districts in District Reference Group A (the others are Easton, New Canaan, Redding, Ridgefield, Weston, Westport, and Wilton). The school's sports teams have won numerous state championships. Darien is known for its competitive football, lacrosse, ice hockey, field hockey, volleyball, and track teams. A tradition at the school's graduation ceremonies is to present honorary diplomas to school teachers or administrators who are retiring. In 2007, they were presented to a school counselor and school librarian.

The three grass oval fields in front of the school were turned in to turf fields and opened for use at the beginning of the 2016–2017 school year. A multimedia scoreboard, a ticket booth and concession area were also added. The Darien Athletic Foundation conducted the largest crowd sourced project in the town's history by raising private contributions to fully fund the project. After years of public debate with school neighbors, stadium lights were turned on for evening game play on September 14, 2017. A synthetic turf baseball field was installed at the high school in the summer of 2007. The DHS Baseball Field Project raised almost $1 million for the field (along with $1.08 appropriated by the Representative Town Meeting, $306,000 provided by the school district and $20,000 donated by the Darien High School Building Committee). Between the time the new high school building was constructed and the end of the 2006–2007 school year, the baseball field was unfit for use because of drainage problems and use of the field by other sports teams. The school's baseball teams had been playing on fields at Middlesex Middle School and at the Town Hall. In 2008 the turf was completed and played on for the first time.

Darien High School's state renowned theater program, Theatre 308, puts on three or more productions each school year, ranging widely in scope and time period. The Fall Drama is intellectual, contemplative, and intimate, while the Spring Musical is often a large scale production targeted at the broader Darien community. Theatre 308's numerous Student Productions in the late spring are innovative, witty, and an all around great time, offering a chance for students to fill the roles usually reserved for faculty members, such as the director. However, the Student Productions are not the only opportunities for DHS students to fill major production roles, as both the Drama and the Musical encourage students to serve as Stage Managers as well as technical designers for Sets, Costumes, Lights, and Sound. The Drama is especially well known for its use of extensive original music composition, direction, and live performance in many of its past shows. The organization as a whole has won numerous HALO Awards for its outstanding lead cast members, powerful ensemble, and amazing direction team, as well as several Sondheim Awards in similar categories. Its shows, ranging from Kiss Me Kate to Metamorphoses to Chicago to The Curious Incident of the Dog in the Night Time, are beloved by the Darien public and widely attended.