Typically, Poetry Week kicks off with a day of guest poet performances in the Upstairs Theatre, followed by two or three days of writers' workshops that take place in East Library and are lead by guest presenters. The week culminates on Friday with the all-school Open Mic during each lunch period in East Library.

Past performers and workshop presenters have included Adam Gottlieb, Carlos Cortez, Jim Flanagan, Kevin Coval, José Olivarez, Idris Goodwin, Ross Gay, Parneshia Jones, Rachel Jemison Webster, Natalie Rose Richardson, Kweku Collins, Dina Elenbogan, Tony Trigilio, Kuumba Lynx, and former National Youth Poet Laureate Pat Frazier.

Jim Flanagan and the annual Poetry Week had a ten year embrace. With his New Jersey accent and his enthusiasm for the possibilities of every young person, Jim would come to Evanston each spring for the inspiration of the Evanston students and school members who would elevate all his hopes for the nation the students would help create. The students called writer and Ph.D. Jim “Doc”. He called them astounding, brave, talented, creative, forceful, honest. In his view, the students who wrote, who read, and the teachers, school workers and visitors who came together for the events of each week rumbled with the force of poetry's best element: honest beauty. Upon his return to New Jersey each year, until his sudden death in 2012, Jim sent notes, encouraging letters and ideas that always showed how much he admired the students and how impatient he was for the coming of the next Poetry Week.

In many ways, Carlos Cortez came to Poetry Week as the eternal sophomore, the confident, creative thinker who had more trust in his own principles than in any old traditions. Though using a cane, the hair of his flowing mustache gray, he had mischief and boldness in his poetry and in the wood and linoleum block prints that flowed inexpensively from his home press onto the walls of East Library and many Evanston homes. From the top of his battered, broad-brimmed hat to the toes of whatever shoes he favored that day, Carlos Cortez was a believer in justice, something that he would help instill in what the students heard and in what they wrote. The students made his eyes sparkle, while they made the years drop from him as, together, they took up the Poetry Week task of explaining a complicated world that could be changed by thought, courage and art.