This paper examines The Negro Motorist Green Book, an annual travel guidebook for African American travelers published by Victor Hugo Green from 1936 to 1966, and its significant role in the rise and development of black automobility in the era of Jim Crow laws in the United States. At the height of racial segregation, early 20th century America also witnessed the massive growth and expansion of the automobile industry which transformed the transportation system and provided new avenues for mobility. Despite pervasive social, cultural, and legal regulations and constraints rooted in white supremacy, African Americans traveled across the nation in their newly purchased automobiles. Moving away from the back seats of racially segregated buses and trains, African American motorists dreamed of the freedom that automotive travel could offer even though it came with the constant threat of physical violence such as lynching in Sundown towns. Research on The Negro Motorist Green Book which recommended African American travelers safe places to stay, eat, and refuel provides an opportunity to explore the evolution of African American traveling culture from the 1930s to 1960s, a period when Black mobility emerged in tandem with the rise of automobile industry. The Negro Motorist Green Book not only facilitated African Americans’ ability to travel without aggravation, but it also became a political tool that supported the Civil Rights Movement, which ultimately helped to repeal Jim Crow Laws. By analyzing the cultural history of black travel and the trajectory of black mobility during the Jim Crow era, this paper aims to present the racial discourse as well as the struggles and resistance of African Americans seeking to move forward in a fractured nation.