Caitlin Cary was the youngest of seven siblings (all older brothers). Her entire family was involved in music to some degree, with her parents' love for singing and her father's interest in building instruments. She had begun to play the violin at age five, but put it aside as a teenager. In addition to the violin, she also played her father's harpsichords, where she wrote some of her own songs.
Cary went to college at the College of Wooster in Ohio. She began working on a degree in English. During her college time, she picked up playing the violin again, and she formed a small 'jokey' band called Garden Weasels. After graduating from the College of Wooster, she enrolled in the graduate program in creative at North Carolina State. During this time, in 1993, musician Ryan Adams contacted Cary and asked her if she would play violin in a band that he was starting. Cary agreed to join, and they formed Whiskeytown.
Caitlin is currently pairing up with Matt Douglas who is the lead singer and songster for The Proclivities. They paired up to perform in Raleigh's annual Love Hangover show, which features a male/female duo singing love song covers. They enjoyed singing together and went on to create the group Small Ponds. An EP was released on Last Chance Records in September 2010.