Rural residents in need of health care face many challenges. In 2009 the Leona M. and Harry B. Helmsley Charitable Trust created the Rural Healthcare Program to improve access to and quality of care in areas of the upper Midwest challenged by health care workforce shortages and low population density. The program has focused its efforts on telehealth in seven upper Midwestern states. Since 2009 the Rural Healthcare Program has approved $22 million in grants to eighty-five rural hospitals to implement eEmergency services. The service’s videoconferencing technology connects rural emergency department staff with emergency physicians and nurses located at the service’s “hub.” Initial analyses indicate that eEmergency has helped participating rural hospitals increase patients’ access to specialists, increase the use of evidence-based treatment, decrease time to transfer a patient to a facility able to provide a higher level of care, and reduce unnecessary patient transfers. This article describes the health care challenges rural communities face and the telehealth projects supported by the Helmsley Trust’s Rural Healthcare Program.