This paper begins with an overview of the state of the art in the design of multi-story mass timber structures and their lateral systems in low to moderate seismic regions. Boston, MA has been chosen as the location for a feasibility analysis of 8-, 12-, and 18- story mass timber structures. These building prototypes are used to compare the structural and environmental efficiencies and tradeoffs of replacing conventional concrete cores with mass timber braced frames and steel-timber hybrid frames. The lateral resistance of prototype configurations is evaluated through numerical analyses to understand in more detail the characteristics of an efficient mass timber lateral system. Finding an optimal timber gravity system configuration is followed by examining lateral resistance of the prototypes. The resulting designs demonstrate a practical approach to assist designers in selecting a lateral system during the early stages of conceptual design. This research was conducted in parallel with a related study for implementation of mass timber in affordable housing in Boston, enabling a comparison between composite systems and all-timber structures.