A new team of Roadtrippers shares a desire to search for something bigger in life. Brooklyn, a self-proclaimed dreamer who left an unfulfilling job in New York City to move back in with her parents and eight siblings, hopes this Roadtrip will "jumpstart" her life. Elliott, a former high school English teacher, gets out of the classroom to explore a life around education, community and creativity. Nekeed escaped a rough childhood in Yonkers, N.Y., where he lost a brother to gang violence. Now, as the first male in his family to graduate college, Nekeed wants to define his next steps in life. At the New Skete monastery in New York, they interview Brother Stavros, co-founder of the monastery; he also works with its famous German Shepherd breeding program.