The Town of Holbrook's first settlers in 1634 were the Cochatos. In the year 1640, Holbrook was incorporated as part of the newly formed Town of Braintree. Along with the Town of Holbrook, other portions of the Town of Braintree separated in 1793 to form the new Town of Randolph, in which Holbrook was known as East Randolph. On a leap year day of February 29, 1872, the village of East Randolph separated from the Town of Randolph and was incorporated as the Town of Holbrook. The town uses this unique birthday in which, it will be "forever young" as an opportunity to gather and celebrate with friends both old and new. At the time of its incorporation, Holbrook was a leading center of boot and shoe production in the United States.