In March 2020, the unprecedented disruptions of the COVID-19 pandemic caused the school to transition to remote learning for the remainder of the academic year.

[6] For the 2006–2007 school year, DSHS tenth-grade students ranked fourth in English and math among their peers on the Massachusetts Comprehensive Assessment System (MCAS) exam.

The school offers sports including American football, soccer, cross country, golf, field hockey, basketball, alpine and Nordic skiing, swimming, baseball, softball, lacrosse, indoor and outdoor track and field, tennis, ice hockey, gymnastics, and sailing.

[8] A DSHS student project officially represented MA State at the International Science and Engineering Fair hosted by Intel in 2006.

[citation needed] The school's Drama Department puts on two productions each year: an autumn play and a spring musical.

The program's music director is Geoffrey Herrmann, the choreographer is Claire MacKay, and the conductor is Ardys Flavelle.

The program is supported by the local community through organizations such as Friends of the Performing Arts, The Mudge Foundation, The Dover-Sherborn Education Fund, and Len Schnabel of DesignLight.

Productions include: Children of Eden, Joseph and the Amazing Technicolor Dreamcoat, Fiddler on the Roof, Seussical, The Importance of Being Earnest, Godspell, The Odd Couple, Anything Goes, Once Upon a Mattress, The Crucible, Pippin, and West Side Story.

Some of their most well-known musical performances include Mamma Mia, Children of Eden, and Les Miserables.

In the past, the Boys and Girls Swim & Dive program has been shared with Medfield High School.