It all started with England’s economic struggle and hunger for power, this is the main reason why the British decided to embark in a journey to the new world. These people were looking for a better chance in life and opportunity to own a piece of land in the new world. That is how this group of people guided by John Smith arrived to America. Joint stock companies such as the Virginia Company of London were interested in the new world. As consequence, Jamestown was born and with it a new hope for the British. This first colony consisted of 104 New Englanders that some settle close to the river meanwhile others far from it. At the beginning life was tough for the colonists who suffered from lack of goods until the Native Americans showed them how to plant the crops and shared their food. They lived peacefully for a while, although, this arrangement did not last for long. The British became aggressive and wanted to enslave the Native Americans and take their land. As consequence, the Native Americans attacked the British to protect their land for several years with no success. One of the main reasons why the Native Americans did not succeed in protecting their land was the diseases that colonists brought with them. Furthermore, colonists keep coming to the new world and more colonies are founded. As result, the New England colony is founded by a group of puritans and separatists that do not believed in the England church. The purpose of this paper is to compare the colonies of Chesapeake and New England, which one had more freedom and greater stability. First, the Chesapeake region succeeded because of two key elements, tobacco and peace with the locals. Tobacco product produced good revenue for England and people who grew it became wealthy. As people became wealthy, more colonists wanted to come to the new world in search for wealth. But this could not be possible thanks to John Rolfe for the audacity to make peace with the local Native Americans in the region. That is how The Powhatan Confederacy was born allowing ex