Our ultimate goal is to prepare each student for a more traditional program that fits his or her academic, social and emotional needs.

While the average student spends three or four years at TSS, each child's enrollment is based on their needs and specific learning profile, as well as the grade into which they will transition. 

How will I know when my child is ready to transition?

Many factors go into determining when it is time to start the transition discussion with parents, including:

  • Academic advancement based on key metrics
  • Input from parents, teachers and advisors
  • Formal and informal testing results
  • Age/grade considerations

When does the transition process begin?

Typically, upon admission to TSS and then ongoing throughout your child’s time here. A formal transition meeting is scheduled in the spring prior to your student’s final year to give you enough time to navigate the admissions process at other schools, but the transition process will be an ongoing dialogue with your child's advisor.

What happens during the transition process?

You meet with your child’s advisor and the director of transitions to review academic testing, current levels of performance and the specific support that your student may need. A range of schools are discussed based on your child’s profile and your family circumstances.

What happens after the transition meeting?

You receive a detailed timeline explaining the process. Your student’s advisor continues to be a resource for you as you pursue your child’ next placement.

What schools do TSS students attend?

Approximately 60% go on to attend independent or parochial schools, while 40% attend public schools. In recent years, TSS alumni have transitioned to schools, including:

Public Schools

  • Darien Public Schools
  • Fairfield Public Schools
  • Monroe Public Schools
  • New Canaan Public Schools
  • Redding Public Schools
  • Weston Public Schools
  • Westport Public Schools
  • Wilton Public Schools
  • Lewisboro, NY, Public Schools


Private Day Schools

  • Chase Collegiate School, Waterbury, CT
  • Easton Country Day School, Easton, CT
  • Fairfield Prep School, Fairfield, CT
  • Fairfield Country Day School, Fairfield, CT 
  • King Low Heywood School, Stamford, CT
  • Lauralton Hall, Milford, CT
  • New Canaan Country School, New Canaan, CT
  • St. Joseph’s High School, Trumbull, CT
  • St. Luke’s School, New Canaan, CT
  • Unquowa School, Fairfield, CT
  • Winston Prep, Norwalk, CT
  • Wooster School, Ridgefield, CT


Boarding Schools

  • Cheshire Academy, Cheshire, CT
  • Cushing Academy, Ashburnham, MA
  • The Eagle Hill School, Hardwick, MA
  • Forman School, Litchfield, CT
  • Gow School, South Wales, NY
  • Harvey School, Kahtonah, NY
  • Indian Mountain School, Lakeville, CT
  • Marvelwood School, Kent, CT
  • Rumsey Hall, Washington Depot, CT
  • Salisbury School, Salisbury, CT
  • Stratton Mountain School, Stratton VT
  • Trinity-Pawling School, Pawling, NY
  • Vermont Academy, Saxtons River, VT




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