The Hip Hop Festival is held annually on Trinity's campus and brings in hip hop artist's from around artists to perform to both Trinity students and the general public, who are free and encouraged to enjoy the event. The Festival was first held in 2006, organized by two Trinity students, Magee Mcilvaine '06 and Jason Azevedo '08. This was in partnership with Nomadic Wax, a company that produces hip hop films and events world wide. It typically occurs over a weekend, with different performances and events on each day.

The founding goals of the Festival were to connect Hartford and Trinity through music, and promote social change through the genre of hip hop. The event features lectures and panels that present a wide variety of educational topics related to hip hop, dance workshops, and graffiti showcases along with the performances done by both local and international artists. The wide interest in the event has led to the establishment of more courses being offered on the hip hop genre at Trinity.

The Festival works closely with Temple, the Trinity chapter of the Temple of Hip Hop, who are devoted to showcasing the genre in a socially conscious way. It is also funded and supported by most of the academic departments and a wide variety of campus clubs and organizations.

The Trinity Reporter, Spring 2007.

The Trinity Reporter, Spring 2009.

The Trinity Reporter, Fall 2017.