[1] It earned a silver medal from U.S. News & World Report in 2017, ranked as the 48th-best high school in Massachusetts.

[7] In the 2010s, the school saw growth in both the number of students taking Advanced Placement courses and in qualifying scores on the exams.

[9] The school's athletic program offers 26 varsity sports with a mascot known as the Marauder,[10] and 26 co-curricular clubs and activities.

As early as 1827, the Commonwealth of Massachusetts required all towns with more than 500 families to establish a free public high school.

[23] A student protest on February 15, 1973, which included a walkout of classes and became known as "Dungaree Day," led to a repeal of the ban.

[24] After moving from Masonic Hall, the classes were held at the Town House for one year until, in 1855, a new school was built on Highland Street and dedicated on December 10.

Special laws were passed by the Massachusetts General Court in 1957 allowing the town to use Stone Park across the street to build a new high school.

[37] In the biology subject exam, Dedham High School has ranked as one of the best in the state, with three students earning perfect scores.

Courses eligible for dual enrollment include English 4, calculus, pre-calculus, world and U.S. history, psychology, biology, chemistry, anatomy and physiology, and environmental earth science.

[9] The town of Dedham has made a substantial commitment to making sure every student has access to the latest educational technology.

[43] Dedham High School participates in the Tri-Valley League (TVL) of the Massachusetts Interscholastic Athletic Association.

In 1946, thousands of fans swarmed the field for about 20 minutes after a Norwood touchdown pass was brought back on an offensive interference penalty.

[50] While they admitted to the paint, they denied being involved with the smashing of 22 windows at Dedham High School on Thanksgiving Day.

[50] Several days after the assassination of John F. Kennedy, the 5th annual torchlight procession and rally was canceled the night before the game, but Dedham beat Norwood at home, 30-0.

[51] As the town of Dedham is the seat of Norfolk County, the school's athletic teams informally used the name "Shiretowners" until 1968.

Most teams play at Veteran's Memorial Field at Stone Park, which was rededicated on Thanksgiving Day, 2011, following a major upgrade and renovation.

[53] A new track and field was installed on the site in 2023, beginning shortly after the June commencement ceremonies; it was completed in the fall.

[58] Town Meeting appropriated $2,500 on September 16, 1895, and the land was graded and developed with a cinder track of .2 miles and a dressing house.

[58] In 1957, the Great and General Court of Massachusetts passed laws allowing the town to use the land to build a new high school.

[28] Tom Arria left the athletic director position in 2010 to take a similar job at a bigger school in Nashua, New Hampshire.

[59] He was replaced by Michael Plansky, who left three years later to join a foundation with which he has family ties that assists veterans with addictions.

[61] Shad Araby was a passionate supporter of Dedham High School athletics and did not miss a football or basketball game in several decades.

[62] According to Massachusetts Department of Elementary and Secondary Education annual statistics, for the 2021-2022 academic year, the demographic enrollment distributions for race, gender and grade level at Dedham High School are as follows: