"[T]he final construction was for a four-classroom building with no basement due to the high water table, all to accommodate 250 students.

This new wave of residents included many well-educated individuals: doctors, lawyers, businessmen, who wanted an education for their children that was as professional as theirs.

[7] In his 1957 annual report, superintendent Edward J. Anderson cited Sputnik as the reason why math and science needed more attention.

In November 1960 The Architectural Forum wrote, “Probably the most talked-about school plant in the U.S. this fall is a collection of five flat-roofed buildings and a big white dome set down in a green pasture some 16 miles west of Boston.

The scope of the project included replacing outdated building systems, updates to lighting, ceilings, flooring, and selected classroom modifications.

[8] In late 2001, the Town of Wayland signed Dore & Whittier Architects to come up with concepts for a larger, modern high school.

With state funding uncertain, the vote to proceed with the schematic designs for the Dore and Whittier proposals was defeated at a Town Meeting.

[8] In 2009, Wayland voters approved a new, $70.8 million, three-building campus designed by HMFH Architects, Inc. Construction of the new school was completed at the end of November 2011, and occupancy by the student body began January 3, 2012.

[4] Students at Wayland High School are required to take courses in English, Social Studies, Mathematics, Science, Wellness, and Fine Arts in order to graduate.

[16] Each year CAPA hosts a College A Cappella Night to help fundraise for Wayland's arts programs.

[18] WHS also has three, student-run a cappella groups: the coed Madrigals, the all-male Testostertones or "T-Tones", and the all-female Muses.

[24] In 2006 Wayland's Varsity football team was undefeated and won the Division 1A State Championship ("The Super Bowl") beating Marshfield High School, 28–0.

[25] The football team traditionally plays against rival Weston High School on Thanksgiving Day.

[29] In 2020 the Warriors beat Boston Latin to clinch the DCL title and were hoping to win a state championship, however the season was cancelled due to the COVID-19 pandemic.

[31] Both the Boys and Girls Lacrosse teams made the Division II playoffs in 2018 and both were ranked as the number one seed in their respective tournaments.

The Girls team won their Division, beating number two seed Groton-Dunstable 17–8, but fell to Bromfield in the state semi-final 13–10.

[32] The Boys team beat rival Lincoln-Sudbury for the first time since 1999 to earn their spot in the playoffs, but ultimately lost during the second round to Concord-Carlise.

[33] In 2009 both the boys and the girls Swim and Dive Teams won Division II State titles becoming the first school in Massachusetts history to win championships in the same year.

[46] In 2023 the WHS Math team won both the Massachusetts and New England meets in the medium school division.

[47] In 2021 the Wayland High School Mock Trial team received varsity status after being founded at least 25 years prior.

[48] In 2022 the WHS Varsity Mock Trial team won the annual Garden City tournament and received a best witness award.