It is a tremendous responsibility of teachers to prepare students for the future workforce by exposing them and providing necessary skills as per current demand of industry. It can be challenging for teachers who receive licensure through a traditional teacher preparation program and have not been exposed to the skills used in the industry. Considering this fact, the Massachusetts Department of Elementary and Secondary Education (MA-DESE) allocated funding for the Perkins teacher externship program that offers a common platform for the professional development of high school teachers by connecting the classroom to the workplace. Through a competitive process, Fitchburg State University was selected to manage and administer the externship program in year 2018. This paper reports the challenges, benefits, and the outcomes of the Perkins teacher summer externship program managed by a team of faculty members of Fitchburg State University. In year 2018, 66 quality lesson plans were submitted by the selected high school academic and career and technical teachers. These lesson plans have been recorded and are available in the "Contextual Learning Portal" to interested teachers who wish to complement and enhance their curriculum. It also helps to educators to formulate effective teaching strategies to achieve maximum outcomes and also assists them in designing and implementing classroom activities, projects, and work-based learning opportunities that will add relevance and meaning to students' classroom learning with the first-hand exposure. This program also provides the opportunity for educators to build a relationship with companies. Moreover, this paper presents benefits of the externship program not only for teachers but also for the externship hosting companies.