Celebrations and News

Westport’s Connections Transition Program Builds Pathways to Independence

Community partnerships, workplace experiences, and innovative technology empower young adults to thrive beyond high school

Now in its fifth year, the Westport Public Schools’ Connections Transition Program continues to support young adults with disabilities as they build the skills, confidence, and independence needed for life after high school. Serving students ages 18–22 who have completed their academic requirements but continue to qualify for special education services, the program blends classroom learning with authentic community experiences across Westport and beyond.

Based in downtown Westport and at Fairfield University, the Connections Program provides instruction in independent living, vocational training, and community engagement. Students participate in cooking groups, travel training, volunteer opportunities, and job placements across a network of more than 20 local businesses and organizations, including the Westport Book Shop, Museum of Contemporary Art, and Fairfield University’s Tully Dining Hall and DiMenna-Nyselius Library.

“The goal of Connections is to help each student develop confidence and independence in real-world settings,” said Michael Rizzo, Assistant Superintendent of Pupil Personnel Services. “Through strong community partnerships, we’re giving young adults meaningful opportunities to practice life and work skills that prepare them for success in the future.”

A recent addition to the program includes the use of virtual reality (VR) simulations that allow students to practice workplace communication and social interaction skills in a supportive environment. Students say the experience helps them rehearse real-world conversations and build confidence before applying those skills on the job.

“Virtual Reality makes it easier for me to practice my conversation skills, which helps me feel more confident at work,” said a student in the Connections Program.

The Connections team, led by Kelsey LaPrad, Special Education Teacher, and Deirdre Flores, Speech and Language Pathologist, has worked to integrate this innovative technology alongside other community-based instruction. Together with trained job coaches and related service staff, the team creates individualized programming designed to meet each student’s goals in education, employment, and independent living.

In December, the program launched a new community partnership through the Pop-Up Holiday Snack Cart at Westport Town Hall. In collaboration with Sweet P Bakery, a nonprofit organization offering training and employment for adults with disabilities, Connections students now help prepare, sell, and deliver baked goods and beverages to Town Hall employees twice a week. The initiative, coordinated with the Town of Westport Human Services Department, offers students valuable experience in customer service, teamwork, and workplace communication—while spreading holiday cheer across departments.

“Partnerships like this reflect what makes Westport special,” said LaPrad. “They connect our students with the community, build mutual understanding, and celebrate the many ways young people can contribute meaningfully.”

The program continues to expand through collaborations with Fairfield University and local employers, offering students access to campus facilities, auditing college courses, and participating in inclusive social experiences with peers.