The relationship between geography and early transfer behavior has received limited empirical attention. In this study, we track six cohorts of university and community college entrants to examine differences in the early pathways they travel through Ontario post‐secondary education (PSE), paying particular attention to how transfer pathway uptake by students in the province's rural north might vary from those in the more urbanized southern regions. Overall, we observe only modest regional differences in early transfer pathway uptake, with parental income proving to be a more constituent predictor of transfer. However, we do find more sizable net regional differences in the propensity that students will drop out within two years of entering PSE, with northern students being significantly more at risk of leaving PSE in their early years.