Freeman attended Milton Academy.[1] As a child she was a competitive skier, and competed in the national championships at the age of twelve.[1][2] By the age of fifteen Freeman was a member of the United States freestyle skiing team.[1] Freeman earned her undergraduate degree at Dartmouth College.[1] Throughout her college career she skied in World Cup competitions and was a member of the Dartmouth sailing team.[1] During her studies at Dartmouth Freeman spent time in Kenya and Mexico.