Dr. Calegari grew up in Connecticut. He received his bachelors degree in psychology from the College of the Holy Cross in Worcester, Massachusetts. He received his medical degree from the University of New England College of Osteopathic Medicine and completed an internal medicine internship and residency program at Baystate Medical Center in Springfield, Massachusetts. He has served as a hospitalist for over 15 years. In 2008, he was elected to the fellowship of the American College of Physicians.