The New England and Chesapeake colonies were both primarily agricultural in nature, but their farms were quite different. This is demonstrated in Never Caught by Erica Armstrong Dunbar, which tells the story of Ona Judge, the slave of George Washington and his family, and her escape to freedom.

Both sets of colonies were designed to provide expansion for British subjects and British trade. Colonies could provide raw materials for manufacturing and markets for the sale of finished goods. That is indeed what the American colonies did for Britain, fulfilling their purposes, at least at first

New England focused on subsistence farming, for the most part. Families held small farms that they worked themselves, growing food for themselves and to trade with their neighbors. The Chesapeake colonies, in contrast, developed larger farms and plantations dedicated to growing tobacco. The slave system took root on the plantations. Many towns, villages, and cities grew up in New England, but there was less of such development in the Chesapeake colonies.

Religion was another major difference between these two groups of colonies. New England was dominated by Puritans, while the Church of England was prominent in Virginia, and Maryland had a blend of Catholics and Protestants. Governmental structures were also different, with town governments taking precedence in New England and colonial assemblies in Virginia and Maryland.

It is rather hard to judge which region was most successful, since they were so different. You could argue that New England's small-town life set the stage for a simple yet prosperous life, or you could focus on the economic successes of the Chesapeake region.