The Negro Motorist Green Book was a publication that offered resources for the Black traveler from 1936 to 1966. More than a directory of Black-friendly businesses, it also offered articles that provided insights for how best to travel safely, engagement with readers through contests and invitations for readers to share travel stories, and even civil rights advocacy. Today, a contemporary counterpart to the Green Book is Black Twitter, where people share information and advocate for their community. By conducting qualitative open coding on a subset of Green Book editions as well as tweets from Black Twitter, we explore similarities and overlapping characteristics such as safety, information sharing, and social justice. Where they diverge exposes how spaces like Black Twitter have evolved to accommodate the needs of people in the Black diaspora beyond the scope of physical travel and into digital spaces. Our research points to ways that the Black community has shifted from the physical to the digital space, expanding how it supports itself, and the potential for research to strengthen throughlines between the past and the present in order to better see the possibilities of the future.