As concerns about climate change increase, many people are calling for reductions in the use of fossil fuels and encouraging a shift to more sustainable and less polluting transportation modes. Cities and urban areas are more concerned because their population currently comprises over half of the world's population. Sustainable transportation modes such as cycling, walking, and use of public transit and electric vehicles can benefit the environment in many ways, including a reduction in toxic greenhouse gas (GHG) emissions and noise levels. In order to enhance the trend of using sustainable modes of transportation, tools, measures, and planning techniques similar to those used for vehicular transportation need to be developed. In this dissertation, we consider four problems in the context of different sustainable modes of transportation, namely, cycling, rail, public transit, and ridesharing. We develop different models to predict bike travel times for use in bike share systems (BSSs) using random forest (RF), least square boosting (LSBoost), and artificial neural network (ANN) techniques. We also use cycling Global Positioning System (GPS) data collected from 10 people (3 females and 7 males) to study cyclists' acceleration/deceleration behavior. Moreover, we develop a continuous rail transit simulator (RailSIM) intended for multi-modal energy-efficient routing applications. Finally, we propose a dynamic trip planning system that integrates ridesharing and public transit. The work done in this dissertation can help encouraging more people to move to more sustainable modes of transportation. / Doctor of Philosophy / As concerns about climate change increase, many people are calling for reductions in the use of fossil fuels and encouraging a shift to more sustainable and less polluting transportation modes. Cities and urban areas are more concerned because their population currently comprises over half of the world's population. Sustainable transportation modes such as cycling, walking, and use of public transit and electric vehicles can benefit the environment in many ways, including a reduction of toxic greenhouse gas (GHG) emissions and noise levels. In order to enhance the trend of using sustainable modes of transportation, tools, measures, and planning techniques similar to those used for vehicular transportation need to be developed. In this dissertation, we consider four problems in the context of different sustainable modes of transportation, namely, cycling, rail, public transit, and ridesharing. We develop different models to predict bike travel times in bike share systems (BSSs) using machine learning techniques. We also use cycling Global Positioning System (GPS) data collected from 10 people (3 females and 7 males) to study cyclists' acceleration/deceleration behavior. Moreover, we develop a continuous rail transit simulator (RailSIM) intended for multi-modal energy-efficient routing applications. Finally, we propose a dynamic trip planning system that integrates ridesharing and public transit. The work done in this dissertation can help encouraging more people to move to more sustainable modes of transportation.