The colonies in the Chesapeake began with Jamestown and was settled in hopes of profit. The settlers had largely come to the New World to seek their fortune, but they hit on hard times during the "Starving Time" of 1609–1610. After this time, they turned to cultivating tobacco, and the colony began importing slaves in 1619. They also developed conflictual relationships with the local Native Americans. The economy was largely based on agriculture, and a pyramidal social structure developed in which a small number of elite planters ruled over a restive class of white indentured servants and black slaves. Bacon's Rebellion of 1676 convinced the white ruling class to impose a rigid color barrier and a harsh form of slavery in colonial Virginia to coerce poor whites into the system and to distance them from slaves. The religion of the Chesapeake was mainly that of the Anglican Church, though Maryland, also in the Chesapeake, was initially founded as a haven for English Catholics.

Massachusetts Bay, on the other hand, was mainly founded so that Puritans could obtain religious freedom. They sought to be an example to the rest of the world, "a city upon a hill." Like the settlers in the Chesapeake, their relations with Native Americans turned contentious as they fought over land. Unlike the initial settlers in the Chesapeake, they arrived in families. Their family life was ordered and ruled by the church and the paternal figures in the family, and young people in Puritan colonies had far less freedom than their counterparts in the Chesapeake. Unlike the colonies in the Chesapeake, the Puritans settled on small farms rather than plantations and also started small industries such as shipbuilding. 

A similarity between both settlements is the hopeful realization intrinsic to them.  One of the primary similarities between the English founding of colonies in both the Chesapeake and those at Massachusetts Bay represents a belief that happiness lies outside of one's established home. Both settlements represent an attempt to expand horizons and boundaries.  Both featured much in way of suffering and pain in the accomplishment of such a vision.  For example, both voyages to the New World were extremely trying.  Many died on the respective voyages and sacrificed a great deal. Yet, this only underscores how important the founding of both sets of colonies were to the settlers who embraced such hardship.  They did not relent in their pursuit of happiness in another setting, and this reality binds them both.

One of the distinct differences between both sets of colonial settlements was their primary reason for being founded.  The Massachusetts Bay colonies were primarily founded for religious freedom.  For example, the Pilgrims settle Plymouth Bay because of their pursuit of religious expression.  Edward Winslow and William Bradford write the document entitled, A Relation or Journal of the Beginning and Proceedings of the English Plantation Settled at Plimoth in New England or Mourt's Relation.  The purpose of this document is to explore the religious leanings of the settlement and publicize it in the hopes of more migration.  This is in stark contrast to the settlement of the Chesapeake Colonies, which focused on primarily on economic wealth.  For example, Jamestown in Virginia was founded on a charter from the Virginia Company of London.  It is founded for the growth of business and economic wealth.  Gold, silver, and other resources were the primary focus of discovery in Jamestown. Once tobacco was discovered, this became the cash crop of the region and provided the ability to generate wealth and develop the accumulation of material goods from the region.  

Both colonial discoveries were driven by a dream to establish a new life away from England.  The sacrifice in the form of suffering and death that took place on the voyage over to the New World and in the initial start up of life in both serve as testament to this reality.  This binds both settlements as representative of the possibility of what can be that lies at the heart of all colonization.  The reason and motivation for founding becomes where this vision of conditionality and promise reflects divergence.