This study examines how a group's dynamic changes under the influence of different leadership styles, and determines what leadership style works best in a large group expedition. The main question identified was "What roles can a leader play in affecting the dynamic of a large group while partaking in a field expedition?" The following research questions were addressed: (1) How can a leader create a positive group dynamic while facilitating an outdoor experience?; (2) How does leadership affect group dynamics?; (3) How does leadership and decision-making interconnect within a positive group dynamic?; (4) Which leadership style works best for various situations in the field?; and (5) What are the barriers and pathways for each leadership style? Data was collected to draw a connection between leadership styles and their affects on the group dynamics of large groups during outdoor expeditions. Findings conclude that it is close to impossible to determine the exact leadership style that would work best in a large group expedition. Groups of any size are incredibly diverse and unique. It is hard to classify and even harder to satisfy those needs and wants. The leadership style that would work best in upholding a positive group dynamic would be a dynamic leadership style. A leader should be able to mould to the group given to them, demonstrating the ability to choose from a number of leadership styles and then applying it appropriately to the group.