Older individuals living on the streets of our urban cities are a unique sub-group of the homeless population. No studies have been published about these elderly “rough sleepers” who face daunting obstacles to health care while facing a litany of health risks on the streets that are magnified by the physical and mental limitations of advancing years. To improve our understanding of this itinerant group, the Street Team of the Boston Health Care for the Homeless Program prospectively followed 30 individuals aged 60 or older living on Boston's streets for the four-year period from 2000 through 2003. This cohort included 8 (27%) women and 22 (73%) men ranging in age from 60 to 82 years. The average age was 67 years old. At the end of the four year study period, 9 (30%) had died and 6 (20%) were in nursing homes. Despite intense efforts, only 5 (17%) found housing. Seven (23%) were still on Boston's streets after four years, and one was lost to follow-up. We conclude that elderly rough sleepers have high morbidity and mortality and pose significant challenges to programs seeking to provide housing and supportive health care services for this vulnerable sub-group of elderly homeless persons. New and creative housing options are needed, and the delicate issues of competency and guardianship must be addressed.