Getting students to and from school safely is important to us. However, as a regional private school, TSS is not able to provide transportation for students. Many families coordinate with one another to carpool or split the cost of private transportation.

Basic procedures for drop off and pick up can be found below, in addition, complete guidelines can be accessed in the document below and are also emailed to all parents in August when pick-up locations are assigned. Parents should note that they must contact the main office prior to 10:00 AM to notify us of alternate pick-up arrangements for their child.

Please keep in mind that we are located in a residential area and we ask that parents accomodate our neighbors during 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 Procedures

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, not Main Street (across from the Fire Station).
  • When dropping off on Main Street, please let 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.



Dismissal begins at 3:10 PM Monday through Thursday, and at 12:31 PM on Friday. No student shall stay on campus after dismissal without the permission of the headmaster or the child’s advisor.

Main Street Pick-Up Procedures

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 unless assigned to the Trinity Lot.

  • 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.
  • 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.
  • Stay in line and move forward as directed by the staff and watch for pedestrians at all times.


Trinity Lot Pick-Up Procedures (on Center Street)

  • Arrive promptly. Students generally leave the building between 3:10 PM and 3:15 PM, arriving at the parking area shortly thereafter.  
  • Utilize the commuter parking area closest to the train station.  Avoid the Trinity Church entrances and parking area (on right when entering the lot).
  • Park your car facing out to avoid backing out of your space, which may limit visibility and interfere with students’ safety.  
  • School vehicles enter the parking area and proceed in a clockwise direction.
  • Staff drivers only wait a few minutes before returning to the school with any remaining children. If a child’s ride has not arrived at the designated time, the student is returned to the school and parents should pick up on Main Street.