This paper presents a case study of an initiative to create an open dialogue between secondary educators and academic librarians through the establishment of the biennial conference “Bridging the Gap” (BtG). The conference fosters collaboration, promotes professional development, and enhances the continuity of Information Literacy (IL) instruction through three distinct tracks: IL, Primary Source Literacy, and Digital Resources. The IL track focuses on collaborative strategies to enhance IL instruction and address the challenges faced by first-year university students. The Primary Source Literacy track highlights the importance of primary sources and how to integrate them into coursework. The Digital Resources track explores the integration of digital media and artificial intelligence in education. This paper discusses the design, implementation, and outcomes of the conference, offering a model for libraries seeking to host similar dialogues and create connections of their own. One of the most significant outcomes of BtG has been the meaningful connections and improved communication with high school educator partners.