Richard Holbrook was one of the original proprietors of Dorchester in 1635, which town was renamed Rehoboth in 1644 and is known today as Milton. Immigrants from Roxbury and Dorchester were the settlers who founded Springfield. Richard was one of them and at Springfield is where he was made a ‘Freeman’ on 10 May 1648.

Holbrook joined with twelve other Puritan families in the Spring of 1653, in sailing around Cape Cod and settling at Long Island in hopes of establishing a new colony. Long Island at this time was claimed by the Dutch at New Amsterdam. But over the next couple of years so many Englishmen came to the east side of Long Island to settle that war nearly broke out with the Dutch. After heavy negotiations, the Dutch cut Long Island in two and ceded the eastern two thirds to the English.

The colony landed at Oyster Bay on 2 April 1653, where “Richard Houldbrook, Robert Williams and Daniel Whithead purchased from Raskokas, Sagamore of Matinecock and Twenty-one other Indians” the first tract of land which is known today as Huntington, Long Island. This first purchase of land which stretched from Cold Spring Harbor to Northport was bought for the price of six coats, six bottles, six hatchets, six shovels, ten knives, six fathom of wampum, thirty eel spears or muxes and thirty needles.

Holbrook built the first house, and his son Abel, was the first white child born in the new colony.

Four years later the Holbrook’s pack their belongings and move to Milford in New Haven Colony, on 6 February 1657/58, where he is listed as an “After Planter.” Here his Will is signed and dated on 29 March 1670. Richard’s trade was a weaving and in his Will he left his looms to his son Abel. His wife Agnes lived a few more years.