The Health Foundation of Central Massachusetts, Inc. was formally established in January, 1999, with initial assets of approximately $60 million. These assets resulted from the sale of Central Massachusetts Health Care, Inc. (CMHC) a physician-initiated, not-for-profit health maintenance organization (HMO). The trustees of CMHC envisioned a philanthropic organization dedicated to improving the health of the people in the region as a fitting legacy to those physicians who founded and then supported the original organization in 1977. As a conversion foundation, The Health Foundation is bound to apply the assets to continue serving a similar purpose and population, or geographic area as the original HMO.

In order to set the initial grantmaking agenda, the first step entailed an environmental scan of what other health-related programs in the region were funded by the state or area philanthropies. The review allowed The Health Foundation to determine where it could add the greatest value with its limited resources of approximately $2.5 million a year. As a result, The Health Foundation created the Health Care and Health Promotion Synergy Initiative (Synergy Initiative) through which it intended to distribute approximately 80% of its grant funds to a few, 3-5 year projects designed to redress significant health disparities by enhancing systemic access to care and promoting healthier lifestyles with integrated, comprehensive strategies. Also, The Health Foundation created the Activation Fund through which it intended to distribute approximately 20% of its grant funds to support smaller, one-year, discrete projects to generate action beyond the routine. These grantmaking avenues were announced to the region in March 2000 and grants from each fund were first made that year. The Health Foundation also allowed a small portion of its annual grantmaking to be Board Designated, as opposed to solicited, to enable The Health Foundation to participate in opportunistic ventures that did not fit the guidelines for the Activation Fund or the Synergy Initiative.

Since 2000, The Health Foundation has granted over $44 million to organizations in Central Massachusetts through the Activation Fund, Synergy Initiative, and Board Designated grants.