Monday, August 17th, 2026
DHS New Staff Orientation
| Schools and EducationTuesday, August 18th, 2026
DHS New Staff Orientation
| Schools and EducationWednesday, August 19th, 2026
DHS New Staff Orientation
| Schools and EducationThursday, August 20th, 2026
Westport Public Schools PD
| Schools and EducationDHS Staff Professional Development
| Schools and EducationFriday, August 21st, 2026
Westport Public Schools PD
| Schools and EducationDHS Staff Professional Development
| Schools and EducationMonday, August 24th, 2026
Westport Public Schools PD
| Schools and EducationGPS First Day for All Teachers
| Schools and EducationDHS Staff Professional Development
| Schools and EducationNew Canaan Public School Convocation
| Schools and EducationTuesday, August 25th, 2026
Westport Public Schools First Day
| Schools and EducationGPS Professional Learning Day (PLD)
| Schools and EducationProfessional Learning Day
| Schools and EducationDHS Teacher Work Day
| Schools and EducationWednesday, August 26th, 2026
GPS Professional Learning Day (PLD)
| Schools and EducationProfessional Learning Day
| Schools and EducationDHS First Day of School (Students)
| Schools and EducationThursday, August 27th, 2026
Grade 6&9 Orientation (Early Release)
| Schools and EducationFirst day of School
| Schools and EducationFriday, August 28th, 2026
GPS First Day for All Students
| Schools and EducationMonday, September 7th, 2026
Labor Day – Schools closed
| CelebrationFriday, September 11th, 2026
Rosh Hashanah - Schools Open
| CelebrationSaturday, September 12th, 2026
Rosh Hashanah – Schools closed
| CelebrationFriday, September 18th, 2026
Early Release/Professional Development
| Schools and EducationMonday, September 21st, 2026
Yom Kippur – Schools closed
| Schools and EducationMonday, October 12th, 2026
Columbus Day – Schools Open
| Schools and EducationColumbus Day – Schools closed
| Schools and EducationFriday, October 16th, 2026
Early Release/Professional Development
| Schools and EducationMonday, October 19th, 2026
DHS Elementary Parent Conferences
| Schools and EducationTuesday, October 20th, 2026
DHS Elementary Parent Conferences
| Schools and EducationGPS Teacher Collab - Early Release
| Schools and EducationWednesday, October 21st, 2026
DHS Elementary Parent Conferences
| Schools and EducationThursday, October 22nd, 2026
DHS Elementary Parent Conferences
| Schools and EducationTuesday, October 27th, 2026
DHS Elementary Parent Conferences
| Schools and EducationTuesday, November 3rd, 2026
Professional Learning Day
| Schools and EducationDHS Staff Professional Development
| Schools and EducationElection Day – Schools closed
| Schools and EducationWednesday, November 11th, 2026
Veterans Day – Schools Open
| Schools and EducationWednesday, November 25th, 2026
Westport Public Schools Early Release
| Schools and EducationNew Canaan Public Schools (half day)
| Schools and EducationThanksgiving Recess – Schools closed
| Schools and EducationGPS - Early Release
| Schools and EducationThursday, November 26th, 2026
Thanksgiving Recess – Schools closed
| Schools and EducationFriday, November 27th, 2026
Thanksgiving Recess – Schools closed
| Schools and EducationMonday, November 30th, 2026
Grade 5 Parent Conferences
| Schools and EducationTuesday, December 1st, 2026
K-5 Parent Conferences (early dismissal)
| Schools and EducationWednesday, December 2nd, 2026
K-5 Parent Conferences (early dismissal)
| Schools and EducationThursday, December 3rd, 2026
K-5 Parent Conferences (early dismissal)
| Schools and EducationFriday, December 4th, 2026
K-5 Parent Conferences (early dismissal)
| Schools and EducationMonday, December 7th, 2026
GPS Teacher PLD - Schools Closed
| Schools and EducationTuesday, December 8th, 2026
GPS K-8 Conferences Early Release
| Schools and EducationThursday, December 10th, 2026
GPS Elementary Conferences - Evening
| Schools and EducationTuesday, December 22nd, 2026
GPS - Early Release
| Schools and EducationWednesday, December 23rd, 2026
Public Schools Early Release
| Schools and EducationHoliday Recess - Schools Closed
| Schools and EducationThursday, December 24th, 2026
Public Schools Holiday - Schools closed
| Schools and EducationHoliday Recess - Schools Closed
| Schools and EducationFriday, December 25th, 2026
Public Schools Holiday - Schools closed
| Schools and EducationHoliday Recess - Schools Closed
| Schools and EducationMonday, December 28th, 2026
Public Schools Holiday - Schools closed
| Schools and EducationHoliday Recess - Schools Closed
| Schools and EducationTuesday, December 29th, 2026
Public Schools Holiday - Schools closed
| Schools and EducationHoliday Recess - Schools Closed
| Schools and EducationWednesday, December 30th, 2026
Holiday Recess - Schools Closed
| Schools and EducationPublic Schools Holiday - Schools closed
| Schools and EducationThursday, December 31st, 2026