Before European settlement, the area now known as Holbrook, Massachusetts, like all of New England, had long been inhabited by Algonquian-speaking peoples.
Holbrook was first settled by Europeans (mostly British colonists) in 1710 as the southern part of Old Braintree, and was officially incorporated on February 29, 1872, the last town created from the former lands of Braintree. It was formerly known as East Randolph, being divided from Randolph by track from the Old Colony Railroad line.
Holbrook's development is typical of suburban Greater Boston. In the 18th and 19th centuries, farming and cottage trades, particularly shoe production, dominated the economy. Slowly, the town evolved into a primarily residential community with many residents commuting to work in Boston proper and the primary employment within the town being in service industries.
As was true of many towns in Massachusetts, its residents served during the United States Civil War. Some members of the famed 54th Massachusetts Volunteer Infantry are buried in Union Cemetery. The impact of the War came not only from the residents' direct participation in the conflict, but was also from the need for production of boots for soldiers. It was during the Civil War that shoe production became a significant component of the town's economic life, and production moved decidedly from the home and into factories.
The story of Holbrook's split from Randolph begins in 1871, when pressure had been building in East Randolph for an independent town. After a little "misunderstanding" (according to Randolph brethren, the Eastern group used rather stronger language) about the placement of a cupola on top of Stetson Hall as a vent for the gas lighting, the pot boiled over and East Randolph petitioned to be incorporated as a separate town. 
Holbrook residents again took up arms in the First and Second World Wars. The latter had a great impact on the life of the community. After 1945, demobilization created a building boom and altered the economy and lifestyle across the United States. Holbrook experienced a housing boom and became a largely residential community, in which some service industry provides local jobs, but from which most residents commute to work in Greater Boston.
Holbrook once held the Baird and McGuire chemical plant, which in 1982 was added to the EPA National Priorities list. Listed as the 14th worst Superfund site, cleanup work began immediately. As of June 17, 1997, the EPA concluded primary cleanup operations at the site. Efforts included the incineration of 248,000 tons of soil, including sediment dredged from the Cochato River. Total cost was approximately 133 million dollars, including the construction of a water treatment plant that is still in operation. 
In February 2009, the Boston Globe listed the Holbrook Town Forest as the choice location in Holbrook.
Holbrook Junior-Senior High School has been named three times as one of the ten most improved schools in Massachusetts on MCAS, the statewide tests taken by all public school students in Massachusetts. Principal Jill Delsignore who served the community of Holbrook for over 30 years as teacher, Holbrook Education Association officer, department head, assistant principal and principal was the administrator when Holbrook was noted in early 2000 on two occasions and Superintendent/Principal Joseph Baeta was the leader when Holbrook was again recognized in 2010.