In the years following the settling at Plymouth, several attempts were made to establish settlements on the shores of Massachusetts Bay for the purpose of fishing and trade. Grants had to be secured from the Council of New England. In 1622, Thomas Weston, a London merchant, sent out a party of about seventy men, mostly a disorderly gathering from the streets of London, to form a settlement at Wessagussut (Weymouth), about twenty-five miles north of Plymouth. The settlement failed to prosper. After one year of inciting Indian troubles and other improprieties, Weston abandoned the settlement and the group happily returned to England. Robert Gorges took over the abandoned post with his own company and from it other isolated settlements began. William Blackstone settled in Shawmut (Boston), Thomas Walford landed in Mishawum (Charlestown), and David Thompson located on the island that bears his name today, Thompson's Island.
Samuel Maverick had chose to settle on a little hill that faced the inner harbor at the confluence of two rivers, an ideal place to set up a trading post. The hill contained fertile ground, practicable for farming and had many fresh water springs. Maverick made his settlement in 1624 and built a fortified house, the first permanent house in Massachusetts (It is believed this house was located near the beginning of the pier on Admiral's Hill). In "A Brief Description of New England" written about 1660, Maverick says: "One house yet standing there which is the Antientist house in the Massachusetts Government, a house which the year 1625 I fortified with a Pillizado and flankers and gunnes both belowe and above in them which awed the Indians who at the time had a mind to cutt off the English."
There is not too much information known about Samuel Maverick and much of it is conjecture. He was born to the Reverend John Maverick, an Episcopalian minister, and Mary (Gye) Maverick in 1602. Samuel Maverick came to America in 1624 the same year he settled Winnisimmet. In 1628 Samuel Maverick married Amias the widow of David Thompson. Amias inherited all David Thompson's property holdings and influence. Through his marriage Maverick acquired these holdings, influencial position and Noddle's Island. Amias was older than Samuel and had one son John Thompson. This marriage brought three children, Nathaniel, Samuel and Mary. Maverick was granted property rights to all of modern day Chelsea except Prattville. In 1631, the first ferry in the state and possibly the country, was granted permission to run from the Maverick farm to Charlestown and Boston. Maverick sold all his Winnisimmet holdings, except his personal farm, to Richard Bellingham in March 1635 and moved to Noddle's Island.
In 1634, Richard Bellingham came from Boston, England to Boston, Massachusetts and was appointed Deputy Governor of Massachusets in 1635, the same year he purchased Winnisimmet. He had a town house on Tremont Street in Boston and used one of Maverick's houses for a summer home. Bellingham had the idea to run Winnisimmet like the manorial estates of England. He divided his land into four farms and leased out each farm to a tenant farmer. The farms became known by the names of the tenants. Originally named the Smith, Rice, Townsend and Senter farms, finally became the Williams, Shurtleff, Cary and Carter farms.
The area around Powderhorn Hill was still heavily forested and unsettled. This was the largest of his farms and it was here that Bellingham built his hunting lodge in 1659, the first and original part of the Bellingham Cary House that we know today.