Getting students to and from school safely is important to us. However, as a private independent school, TSS is not able to provide transportation for students. However, many families coordinate with one another with carpools or split the cost of private transportation. Contact the Main Office for more information at 203.254.2044.

Basic procedures for drop-off and dismissal can be found below, in addition, complete guidelines will be emailed to all families in August closer to the first day of school. Parents and Guardians must provide all arrival and dismissal instructions for their child through the app School Dismissal Manager.

Please keep in mind that we are located in a residential area and we ask parents to respect the peaceful surroundings of our neighbors during these busy times of the day. Please avoid blocking driveways, turn off your engine when waiting, and avoid parking directly in front of the fire hydrant. During pick-up and drop-off staff members are always outside, rain or shine, to help direct traffic. 

Drop-off Arrival Procedure

Students should be dropped off no earlier than 7:50 AM when staff are out in front of the school to welcome them.

  • Please access the school via Pequot Avenue and Chester Place, please do not create parking line on Main Street across from the Southport Fire Station.
  • When dropping off on Main Street, please let your child or children out on the School side to avoid them having to cross the street.
  • Please do not pull up in front of the school until staff members signal that it is safe to do so.


Pick-up Dismissal Procedure

Dismissal begins at 3:10 PM Monday-Thursday, and at 12:31 PM for a half-day dismissal on Friday.

  • At the end of the day students are dismissed in groups as their transportation arrives. Students are to be picked up on Main Street directly in front of the school.
  • Begin to line up next to the one-hour parking sign at the northern edge of the school's property, just beyond the yellow fire hydrant.
  • To ensure a smooth and safe departure, we request that drivers arrive just after 3:00 PM.
  • Access via Pequot Avenue and Chester Place, not Main Street in front of the Southport Fire Department.
  • Stay in line and move forward as directed by the staff and watch for pedestrians at all times.
  • No student shall stay on campus after dismissal without the permission of the headmaster or the child’s advisor.



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