Like most major urban cities, the City of Vancouver has an overall transportation strategy. In January 1996, the City of Vancouver began a broad city-wide public engagement program that eventually led to the Council-approved Vancouver Transportation Plan in May 1997, nearly 15 years ago. While the plan was a great step forward for the City, most action items are completed and many of the targets were exceeded a decade ahead of schedule. Development of a new, longer range plan (Transportation 2040) is now underway to set the City’s sights higher and farther ahead. This paper provides an overview of the regional context and original public process undertaken to complete the 1997 Vancouver Transportation Plan and summarizes some key related planning milestones over the years to follow. The paper then summarizes recent transportation monitoring results, highlighting the significant sustainable transportation progress that has been achieved over the last 15 years. Finally, the paper includes an overview of the development process for Transportation 2040, from its initiation in the Greenest City Action Plan and onward into developing the first active transportation implementation plan. An overview of the plan’s goals and principles, as well as a summary of some of the top policies and actions, are included.