The topic of safe routes to school has been researched since the 1970s, and safe routes to school have been a goal of government programs since 1997. Despite the improvements made because of these efforts, the share of students walking and biking continues to decline. Identified barriers include parents' concerns about safety, the environment, time, and external factors such as traffic, weather, and distance. This research suggests that planners have overlooked two important factors influencing distance: education movements since the 1950s for greater school choice and affordable housing policies. Beyond desegregation, the creation of magnet schools, vouchers, academies, charter schools, and other school options has resulted in growing shares of urban students traveling long distances to school. In Oakland, California, only 49% of students attend school in the neighborhood where they live, and another 10,228 attend 34 charter schools with countywide enrollment. U.S. housing policies have also changed. Construction of public housing has ceased, save for the construction of replacement units. Housing voucher programs are oversubscribed, and individuals with vouchers often change neighborhoods or cities to find a unit. Foreclosures, high prices, and low vacancy rates in cities have also limited housing availability. School and housing policies combined have eroded the economic location theory, in which families balance housing and transportation costs to be near work and good schools. The study uses surveys, time use diaries, and interviews with 70 Oakland parents or caregivers. Results identify the complex choices that affect school travel and offer potential ways for transport, land use, and education planners to coordinate active travel to school.