High schools today have a unique challenge: to equip students with the knowledge and tools they need to prepare for, apply to and enroll in college--all while proving them with digital resources and skills essential for the 21st century. This guide by the Pullias Center's Digital Equity in Education team provides a general overview of what a college-going culture is and how it can be created, with an optimal timeline of college-going activities, starting from eighth grade through the summer after graduation. In addition, the guide offers tips for the digital era, from using online tools to engage students to empowering students to create content that inspires their peers to pursue a college degree.