Understanding why America developed into the nation that it did requires an understanding of its earliest settlements. Understanding the sectionalism that would result in Civil War requires the same. This Venn Diagram, best used after students have learned a little bit about the Massachusetts Bay Colony and the Jamestown Colony, requires students to compare and contrast the characteristics of the two regions. The Venn Diagram includes 23 terms and a Venn graphic organizer. An answer key is also included. The terms include but are not limited to the years of settlement, the leaders of the settlements, the motivations for settlement, etc...This lesson is a good way to get students thinking at a higher level (comparison). It can be used as a whole class period lesson for the lower grades or an intro or half a period lesson for the upper grades.