The school was named for its principal benefactor, philanthropist Theodore Lyman, who served as mayor of Boston, Massachusetts from 1834 to 1836.

Lyman School was situated near Lake Chauncy in the town of Westborough, on Powder Hill, off State Route 9.

The farm remained a principal means of support for the school until about 1955 when the economy of the region became predominantly industrial rather than agricultural due to the placement of major companies along State Route 9.

Several famous criminals attended the Lyman School, one of them being the Boston Strangler, Albert DeSalvo.

In the late 1950s, it became difficult to find cottage parents willing to work such long hours, so several changes were made.

In the 1950 to 1960 era, the cottages were Lyman Hall, Chauncey, Overlook, Sunset, Hillside, Wachusett, Worcester, Elms, and Oak.

[3][4] The Lyman School for Boys has a less than pacific social history ranging from its nearly complete destruction by arson in its early years to runaways who were never caught nor heard from again.

[3] During the 1960s, college students from Harvard University in Cambridge, Massachusetts, including Ted Todd, regularly visited boys at Lyman School.

In the fall of 1964, Sherrie Connelly, then a student at Smith College in Northampton, Massachusetts, visited the school with Todd and developed a Christmas project involving about 100 college students who sent Christmas cards and gifts to boys at Lyman School.

During the administration of Governor Endicott Peabody (1962–1965), various trade unions complained that maintenance of state-owned buildings at the Lyman School was being performed by non-union labor.

[6] The institution was closed in 1971 by the Massachusetts Department of Youth Services just two years after Governor Francis Sargent appointed Jerome G. Miller as its Commissioner.