Three college grads travel across the country to speak with Leaders who have defined their own Roads in life. Arriving in Philadelphia, the team meets with Rosemarie Certo, the owner of Dock Street Brewing Co., where they get a taste of her award-winning beer and her passion for the craft. Next, they travel to Chicago to speak with Grammy Award-winning children's folk singer Ella Jenkins, who teaches the Roadtrippers a song. The team also meets with Paolo Davanzo and Lisa Marr-a happy-go-lucky couple that expresses their love for filmmaking by helping students through affordable film and media arts classes.