Cait started swimming for her local swim team when she was eight years old, and entered her first triathlon at thirteen. She won her first race (Worcester Youth Triathlon) in flannel shorts and on her mother's bike. In the years that followed, she joined her high school swim and track teams, captaining both during her junior and senior years. Throughout high school Cait raced frequently, consistently winning her age-group. During her sophomore year in college she began taking her training and racing much more seriously. Cait spent the next several years competing in collegiate and ITU-format events before tearing her ACL and meniscus in 2006.