The Internship Program at New Fairfield High School is offered through the regional collaborative known as Education Connection which is able to offer programs that individual schools might not have the resources to develop and sustain on their own. The Internship Program is currently funded by the Western Connecticut Superintendents' Association and involves students from all the school districts within its jurisdiction.

Internships in the business and medical fields are available to Juniors and Seniors at New Fairfield High School each year. Students work in a professional setting one day a week for three hours after school. They have the opportunity to be employed in two separate job placements in a year, affording them the opportunity to “sample” several careers. Students also attend monthly classes designed to help them to learn the “soft skills” necessary to succeed in the world of work., interpersonal skills, professional behavior, how to work effectively in teams, etc. In addition to teaching the students important skills, the classes also give New Fairfield students the opportunity to meet students from all the districts in the region who are participating in the program.