One of Gilman's most impactful community service programs was Upward Bound. A federally funded program, Gilman Upward Bound (then called Operation Challenge), was founded by Gilman faculty Redmond C. S. Finney '47 and William B. Campbell '52 in 1967 as a college preparatory program that provided academic and social support to students from the City of Baltimore.

The first Operation Challenge cohort included 51 students from city schools and 13 Gilman students from the Class of 1968. The program consisted of a six-week summer school for students, followed by tutoring, special programs, and bi-weekly Saturday reunions throughout the school year. Teachers that first year included Gilman faculty Frank Pine, Jerry Downs, Bill Andrews, Jim Riley, David Allan '64, and future Gilman faculty William Greene, who was then still a teacher at Gwynns Falls Junior High. In 1969, Mr. Campbell and Mr. Finnney would convince Mr. Greene to come work at Gilman full time, and in 1970, he succeeded Mr. Campbell as director of Gilman Upward Bound.

Over the years, Upward Bound would expand to offer an extensive curriculum, with courses ranging from literature to calculus. Enrollment also expanded; by 2001, 110 students enrolled in Gilman's Upward Bound program. Gilman students would participate in the program over decades, serving as tutors and classmates, up until its last year of operation in 2004. Today, the legacy of Upward Bound continues with Gilman partnering with several long-term community projects, including Bridges and Middle Grades Partnership. 

In the 1967 Bulletin, Mr. Finney, then head of the history department and head coach of the varsity football team, described the founding of Upward Bound as follows:

"It all started in the early spring of 1966 when Bill Campbell and I began to explore the idea of establishing a summer program. Our original intention was to conduct an academic strengthen­ing and enrichment program for the duration of the Gilman Summer School. Our thinking had not progressed to a consideration of academic year follow-up, nor did we originally envision working with the same youngsters for more than one summer session. As later developments unfolded, and we became exposed to other programs and new ideas, we realized that one short summer experience on the Gilman campus might do more harm than good. When you try to open a door for someone, you have to keep the door open and to make secure the gains in terms of motivation and new excitement.

Originally we asked the Office of Economic Opportunity for information and possible funds, and they directed us to the Baltimore Community Action Agency. We were told that the chances of obtaining funds locally were not good because of a cutback in appropriations, and we decided to go to Washington to talk with Upward Bound. Even though they could not be encouraging, we decided to submit a proposal. It worked out that we were among the last programs to be funded by O.E.O.

The criteria set up by Upward Bound provided us with our greatest enlighten­ment. Their program requires consecutive summer sessions and academic year follow-up. Once a student enrolls in Upward Bound, he remains a part of it until he enters college or some form of post-secondary school education. Increasingly we realize the good sense of this criterion."

Read Mr. Finney's full reflections from the 1967 Bulletin.