Over the course of the past few decades, technology has shaped the way people interact, work, learn, and retrieve and disperse information. The advent of the 21st Century includes new forms of knowledge and information, requiring tools and skills previously unseen by generations of learners. New tools are meant to be used for expansion of knowledge rather than replacement, and 21st Century schools must equip students with these skills in order for them to be competitive in the new global workforce. Twenty-first Century skills have altered the landscape of education, in that they demand competent, knowledge-based leadership which values the role of knowledge creation. Schools have had a common purpose: to be technical schools, not constructivist ones. Recent standards reform was designed to continue this type of schooling. However, changing needs in society have led to the implementation of 21st Century skills to engage students in learning. The goal of 21st Century schools is to provide students with both a constructivist organization in which teachers construct their own responses to problems in the polis and classroom practices that let students engage in constructivist Web 2.0 activities. This researcher chose four schools in one regional district. The regional district is not a designated government unit; it refers to a cluster of school districts in a specific geographic location. The researcher's purpose in this case study was to investigate how educators and school systems engage both school adults and students in 21st Century education in one regional district on Long Island. The work of Adria Steinberg (1998), Frank L. Smith (1991), The Partnership for 21st Century Skills (2002), and Thomas Popkewitz (1982) were used to develop a conceptual framework to analyze the findings of the study to determine the level of engagement in patterns of instruction, organization, governance, and assessment in relation to the patterns envisioned for 21st Century schools. This study parallels a study performed by Sean B. Fox. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]