Reverend Stephen Gray founded the Hopkinton Education Foundation during the 1991-1992 school year to give Hopkinton citizens and businesses a way to fund innovative educational opportunities for the town’s students. Its purpose was to supplement the school system’s budget. Community meetings were held to solicit interest and input, and education foundations from around the state and country were researched to understand how they were formed and operated.

In 1992, a Board of Directors was established, by-laws were created, and non-profit status was established. Supporting committees were then formed and the Hopkinton Education Foundation began to grow. The Hopkinton Education Foundation decided to fund creative projects that were not normally financially supported by the school budget but could still have the greatest impact on the largest number of students. Grant awards were initially limited to $1,000 for individual teachers. Grant processes and guidelines were developed as well as criteria to evaluate grant applications. In the fall of 1992, fundraising efforts began with community solicitation. As a result, the Hopkinton Education Foundation raised $12,000 during the 1992 – 1993 school year, its first year of official operation. Eleven thousand dollars in grants were awarded during surprise visits made to teachers at their schools.

In the 1993 – 1994 school year, the Hopkinton Education Foundation more than doubled the funds it raised the year before by raising $25,000 and awarding $22,000 in grants.

In February, 1994, the first Hopkinton Education Foundation Dinner Dance was held.