Commencement is the ceremony at the end of each academic year when graduating students receive their diplomas. Typically occurring mid- to late-May on Trinity's Main Quad, the ceremony features speeches and awards given by and to a variety of students and staff. These awards include Trustee Awards for faculty and staff, as well as awards presented for Student Excellence. It is also traditional for graduating seniors to deliberately step on the Roosevelt Plaque during the ceremony, as doing it before commencement is thought by students to be bad luck.

The ceremony has gone through changes throughout Trinity's history. Commencement originally was held on the first Thursday of August, but changed in the 1850s to the last Thursday in June in order to allow for more comfortable weather. This change in the month also came with the change to fully complete the ceremony in one morning session, rather than splitting it up into one morning and one afternoon session as it had been in previous years. The date consistently was placed in June for over 100 years, with the switch to May ceremonies occurring in the 1970s.

The location of commencement has also changed. In the early years of the College, when it was still located at the old campus, the ceremony would start by the (old) Chapel at 8:30 a.m. At 9:30, the group would leave campus and head to Asylum Street, where they would stop at Bishop Brownell's house and sing “Auld Lang Syne.” The group would then continue to Main Street where Christ Church was located, as this was where the main ceremony was held. The church, along with Trinity students and staff, was also often full of children from the local community, as many Hartford schools gave students the day off on Trinity's commencement day.

The last ceremony to be held in Christ Church was in 1860. It was moved to St. John's Church in 1861, but due to the large number of people the space had to hold, the ceremony was moved again the following year to Allyn Hall. The commencement ceremony of 1878 was the last one to be held at the old campus, and the President's reception for this last old campus commencement took place in the newly built Seabury Hall on the new campus.

Due to the smaller student body in the College's early years on the old campus, each graduating senior was able to receive his degree directly from the school president and shake his hand. Though inconsistent throughout the decades, it was also traditional for each graduate to touch “The Book.” This book, according to college legend, was President Brownell's small record journal that he used in place of a Bible during Trinity's very first commencement ceremony. He had wanted a Bible for each senior to touch as they graduated, but forgot to bring one; the journal was used in its place. The tradition of seniors touching the Book at graduation was reinstated later in Trinity's history by President G. Keith Funston in the 1950s.

Other facets of early commencements also included welcoming speeches given in Latin, prayers spoken by the President, and music provided by the choir at Christ Church. Local Hartford bands also supplied music over the course of the day, something that is true to modern ceremonies.

Degree abbreviations: DD – Doctor of Divinity; LHD – Doctor of Humane Letters; DHum – Doctor of Humanities; LittD – Doctor of Letters; LLD – Doctor of Laws; ScD – Doctor of Science; DFA – Doctor of Fine Arts; DM – Doctor of Music; DST – Doctor of Sacred Theology; DPH – Doctor of Public Health; JCD – Doctor of Canon Law; MA – Master of Arts; MFA – Master of Fine Arts; MLitt – Master of Letters; MM – Master of Music; MS - Master of Science; BA – Bachelor of Arts; BM – Bachelor of Music; BS – Bachelor of Science

• 2023 - Nicole Hockley, '92, Co-founder and CEO of Sandy Hook Promise
• 2022 - Raja Changez Sultan, '72, DFA, Painter, poet, journalist
• 2021 - Jeffrey A. Flaks, LHD, Hartford HealthCare President & CEO
• 2020 - Will McCormack '96, executive producer, director, screenwriter, actor (The delayed commencement ceremony was held in June 2022.)
• 2019 - Samuel H. Kennedy, '95, LHD, Executive, President & CEO of Boston Red Sox
• 2018 - Johnnetta Betsch Cole, President of Spelman College
• 2017 - Daniel C. Dennett, LHD, Philosopher, writer, and cognitive scientist

Trinity College Commencement Program, 2022.

Trinity College in the Twentieth Century (2000) by Peter and Anne Knapp, pp. 232-233.

The History of Trinity College (1967) by Glenn Weaver, pp. 111-112, 134-135, 186.