This dissertation examines the interaction of the built environment, travel behavior, and technology usage among older adults. Decades-long transportation policies favoring vehicle owners have made many older adults disadvantaged in daily travel. Studies and policies specifically addressing older adults’ travel needs do not keep pace with the increasing number and diversity of the aging population. To fill the research gaps, I conducted a series of empirical studies to analyze the travel pattern trends of older adults in order to identify their difficulties in travel. I first examine how older adults travel differently since 2000. Descriptive analysis and a quasi-panel design using the National Household Travel Survey show that those aged 55-74, the baby boomer generation, did not have higher vehicle travel, especially non-work travel, per person, than people at the same age decades ago. Results also show the travel difficulties of low-income older adults. Second, I use cross-sectional and longitudinal data to identify older adults who had difficulties owning and maintaining vehicles. I find that households headed by retirees, those who had lost their partner, and those who lived alone had a higher possibility of living in low-density areas without vehicles. These families also tended to have a decline in vehicle ownership and did not relocate. Third, given the potential role of information communication technology (ICT) in mitigating older adults’ travel difficulties, I surveyed 2,510 older adults, examining the relationship between ICT usage and travel before and during the pandemic. Results show that overall, those who used ICT less also traveled less. In particular, older adults with low incomes and less education, older adults who lived alone, and older African Americans had lower daily vehicle travel and more difficulties using most technology applications. However, health and social technology applications could reduce the difficulties in daily travel for people of color and those with medical conditions. The survey also reveals that age added to the transport disadvantage and digital divide during the pandemic. This dissertation sheds light on transport equity theories, as well as transportation, land use, and technology policies, in order to promote sustainability and equity in an aging society.