SunMonTueWedThuFriSat
30 31 1 2 3 4 5
Sunday August 30 2026
 
Monday August 31 2026
🏈VARSITY FOOTBALL PRACTICEfrom 7:00 am to 9:00 am
Location: Pawling Tiger Stadium at PCMS

Monday,  August  31
7:00 am - 9:00 am
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 8:30 am to 10:30 am
Location: BREWSTER HIGH

Monday,  August  31
8:30 am - 10:30 am
⭐🟥⚽⚽👦🏽👦🏽HOME JV BOYS SOCCER PAWLING VS FOX LANE (SCRIMMAGE)from 5:00 pm to TBD
Recently Updated   Recently Updated

Location: Pawling Tiger Stadium at PCMS

Monday,  August  31
5:00 pm - TBD
🏐VOLLEYBALL PRACTICEfrom 5:00 pm to 7:30 pm
Location: Pawling HS

Monday,  August  31
5:00 pm - 7:30 pm
🏑VARSITY FIELD HOCKEY PRACTICEfrom 5:00 pm to 7:30 pm
Location: Pawling Tiger Stadium at PCMS

Monday,  August  31
5:00 pm - 7:30 pm
Show MenuClick this to show the menu.🏃🏽‍♂️🏃🏽‍♀️VARSITY CROSS COUNTRY PRACTICEfrom 5:30 pm to 7:00 pm
Location: Pawling Tiger Stadium at PCMS

Monday,  August  31
5:30 pm - 7:00 pm
⭐🟩⚽👦🏽(bus at 5 PM) AWAY Boys Varsity Soccer Scrimmage vs. Brewster/Dover AT BREWSTERfrom 6:00 pm to 8:00 pm
Location: Brewster High School

Monday,  August  31
6:00 pm - 8:00 pm
Tuesday September 1 2026
Location: BREWSTER HIGH

Tuesday,  September  1
8:30 am - 10:30 am
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  1
4:30 pm - 8:00 pm
Location: Pawling HS

Tuesday,  September  1
5:00 pm - 7:30 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  1
5:00 pm - 7:30 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  1
5:30 pm - 7:00 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  1
5:30 pm - 7:30 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  1
6:30 pm - 8:00 pm

Pawling HS - Athletic Department Entrance in the back of the school (HS GYM)



Location: Pawling HS

Tuesday,  September  1
7:00 pm - 8:00 pm
Wednesday September 2 2026
Cancelled   Cancelled

Location: Haldane High School

Wednesday,  September  2
TBD
Location: Pawling Tiger Stadium at PCMS

Wednesday,  September  2
7:00 am - 9:00 am
⭐🟩⚽👦🏽AWAY Boys Varsity Soccer Scrimmage @ Nanuetfrom 10:00 am to TBD
Location: Nanuet Senior High School

Wednesday,  September  2
10:00 am - TBD
⭐🟩🚍⚽⚽👦🏽AWAY JV BOYS SOCCER SCRIMMAGE @ NANUET HSfrom 11:30 am to TBD
Location: Nanuet Senior High School

Wednesday,  September  2
11:30 am - TBD
(To be rescheduled)⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ Haldane HSfrom 5:00 pm to 6:30 pm
Cancelled   Cancelled

Location: Haldane High School

Wednesday,  September  2
5:00 pm - 6:30 pm
🏐VOLLEYBALL PRACTICEfrom 5:00 pm to 7:30 pm
Location: Pawling HS

Wednesday,  September  2
5:00 pm - 7:30 pm
🏑VARSITY FIELD HOCKEY PRACTICEfrom 5:00 pm to 7:30 pm
Location: Pawling Tiger Stadium at PCMS

Wednesday,  September  2
5:00 pm - 7:30 pm
Show MenuClick this to show the menu.🏃🏽‍♂️🏃🏽‍♀️VARSITY CROSS COUNTRY PRACTICEfrom 5:30 pm to 7:00 pm
Location: Pawling Tiger Stadium at PCMS

Wednesday,  September  2
5:30 pm - 7:00 pm
🏈VARSITY FOOTBALL PRACTICEfrom 5:30 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Wednesday,  September  2
5:30 pm - 8:00 pm
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Wednesday,  September  2
6:00 pm - 8:00 pm
Thursday September 3 2026
❌ --- Superintendent's Conference DayAll Day
Location: Pawling HS

Thursday,  September  3
(All Day)
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: BREWSTER HIGH

Thursday,  September  3
3:15 pm - 5:00 pm
⭐🟥🏑HOME VARSITY FIELD HOCKEY PAWLING VS SUFFERNfrom 4:30 pm to TBD
Location: Pawling Tiger Stadium at PCMS

Thursday,  September  3
4:30 pm - TBD
🏈VARSITY FOOTBALL PRACTICEfrom 4:30 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Thursday,  September  3
4:30 pm - 8:00 pm
🏐VOLLEYBALL PRACTICEfrom 5:00 pm to 7:30 pm
Location: Pawling HS

Thursday,  September  3
5:00 pm - 7:30 pm
Show MenuClick this to show the menu.🏃🏽‍♂️🏃🏽‍♀️VARSITY CROSS COUNTRY PRACTICEfrom 5:30 pm to 7:00 pm
Location: Pawling Tiger Stadium at PCMS

Thursday,  September  3
5:30 pm - 7:00 pm
(6:30-8:00 PM in HS Team Room and fitness room )🏈FOOTBALL Practicefrom 6:30 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Thursday,  September  3
6:30 pm - 8:00 pm
Friday September 4 2026
❌ --- Asychronous Superintendent's Conference DayAll Day
Location: Pawling HS

Friday,  September  4
(All Day)
🏈VARSITY FOOTBALL PRACTICEfrom 7:00 am to 9:00 am
Location: Pawling Tiger Stadium at PCMS

Friday,  September  4
7:00 am - 9:00 am
⭐🟩🚍🏑AWAY VARSITY FIELD HOCKEY PAWLING @ JJCR (Contest Field)from 2:00 pm to TBD
Location: John Jay High School

Friday,  September  4
2:00 pm - TBD
(To be rescheduled)⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ North Salem HSfrom 4:30 pm to 6:00 pm
Cancelled   Cancelled

Location: North Salem CSD

Friday,  September  4
4:30 pm - 6:00 pm
⭐🟥🚍🎾HOME VARSITY GIRLS TENNIS BREWSTER/PAWLING VS OSSINING HIGH SCHOOLfrom 4:30 pm to TBD
Location: Brewster High School

Friday,  September  4
4:30 pm - TBD
🏐VOLLEYBALL PRACTICEfrom 5:00 pm to 7:30 pm
Location: Pawling HS

Friday,  September  4
5:00 pm - 7:30 pm
Show MenuClick this to show the menu.🏃🏽‍♂️🏃🏽‍♀️VARSITY CROSS COUNTRY PRACTICEfrom 5:30 pm to 7:00 pm
Location: Pawling Tiger Stadium at PCMS

Friday,  September  4
5:30 pm - 7:00 pm
🏈VARSITY FOOTBALL PRACTICEfrom 5:30 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Friday,  September  4
5:30 pm - 8:00 pm
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Friday,  September  4
6:00 pm - 8:00 pm
(To be rescheduled) ⭐🟩🚍🏐🏐AWAY JV VOLLEYBALL PAWLING @ North Salem HSfrom 6:15 pm to 7:45 pm
Cancelled   Cancelled

Location: North Salem

Friday,  September  4
6:15 pm - 7:45 pm
⭐🟩🚍⚽👦🏽AWAY VARSITY BOYS SOCCER PAWLING @ Peekskill HSfrom 6:30 pm to 8:30 pm
Location: Torpy Field

Friday,  September  4
6:30 pm - 8:30 pm
Saturday September 5 2026
🏑VARSITY FIELD HOCKEY PRACTICEfrom 9:00 am to 11:00 am
Location: Pawling Tiger Stadium at PCMS

Saturday,  September  5
9:00 am - 11:00 am
🟥🏈HOME Multi-team Scrimmage FB V PAWLING HIGH SCHOOL from 10:00 am to 1:00 pm

Tentative schools:  

Tri-Valley, Millbrook-Webutuck,  Pawling, Pine Plains-Rhinebeck



Location: Pawling Tiger Stadium at PCMS

Saturday,  September  5
10:00 am - 1:00 pm
6 7 8 9 10 11 12
Sunday September 6 2026
 
Monday September 7 2026
🚫🚫🚫🚫🚫🚫🚫🚫🚫🚫🚫Labor Day (District Closed)TBD
Location: Pawling HS

Monday,  September  7
TBD
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Cancelled   Cancelled

Location: TBA

Monday,  September  7
6:00 pm - 8:00 pm
Tuesday September 8 2026
❌❌❌❌❌❌❌❌❌❌ ❌ --- Superintendent's Conference Day(NO SCHOOL FOR STUDENTS)All Day
Location: Pawling HS

Tuesday,  September  8
(All Day)
⭐🟥🏑HOME VARSITY FIELD HOCKEY PAWLING VS BRONXVILLEfrom 4:30 pm to TBD
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  8
4:30 pm - TBD
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  8
5:00 pm - 8:00 pm
⭐🟩🚍🎾AWAY VARSITY GIRLS TENNIS PAWLING/BREWSTER @ LAKELANDfrom 5:00 pm to TBD
Location: Lakeland High School

Tuesday,  September  8
5:00 pm - TBD
⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ Haldane HSfrom 5:00 pm to 6:30 pm
Cancelled   Cancelled

Location: Haldane High School

Tuesday,  September  8
5:00 pm - 6:30 pm
Show MenuClick this to show the menu.🏃🏽‍♂️🏃🏽‍♀️VARSITY CROSS COUNTRY PRACTICEfrom 5:30 pm to 7:00 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  8
5:30 pm - 7:00 pm
(6:30-8:00 PM in HS Team Room and fitness room )🏈FOOTBALL Practicefrom 6:30 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  8
6:30 pm - 8:00 pm
BOE MEETING 7PMfrom 7:00 pm to TBD
Location: Pawling MS

Tuesday,  September  8
7:00 pm - TBD
Wednesday September 9 2026
FIRST DAY OF SCHOOL FOR STUDENTSAll Day
Location: Pawling HS

Wednesday,  September  9
(All Day)
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: BREWSTER HIGH

Wednesday,  September  9
3:15 pm - 5:00 pm
⭐🟥🏐🏐HOME JV VOLLEYBALL PAWLING VS Riverside HS (cancelled - Riverside does not have a JV team)from 4:30 pm to TBD
Cancelled   Cancelled

Location: Pawling HS

Wednesday,  September  9
4:30 pm - TBD
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Wednesday,  September  9
5:00 pm - 8:00 pm
⭐🟥⚽👧🏽HOME VARSITY GIRLS SOCCER PAWLING VS ARLINGTONfrom 5:00 pm to TBD
Location: Pawling Tiger Stadium at PCMS

Wednesday,  September  9
5:00 pm - TBD
⭐🟥🏐HOME VARSITY VOLLEYBALL PAWLING VS Riverside HSfrom 5:15 pm to TBD
Location: Pawling HS

Wednesday,  September  9
5:15 pm - TBD
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Wednesday,  September  9
6:00 pm - 8:00 pm
Thursday September 10 2026
Meeting for all modified sports teams: coaches and student-athletes after school until 3:45 PMAll Day

Students may be picked up after school or take the 4PM bus home.  (There will be NO practices.  This is only a meeting for students and coaches.)  (Practices begin on Monday, September 8, 2025.)



Location: Pawling MS

Thursday,  September  10
(All Day)
🎾SKILLS VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 4:30 pm
Location: BREWSTER HIGH

Thursday,  September  10
3:15 pm - 4:30 pm
Show MenuClick this to show the menu.⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ Haldane HSfrom 5:00 pm to 6:45 pm
Location: Haldane High School

Thursday,  September  10
5:00 pm - 6:45 pm
⭐🟥⚽⚽👦🏽HOME JV BOYS SOCCER PAWLING VS PORT CHESTERfrom 5:00 pm to TBD
Location: Pawling HS Grass Field

Thursday,  September  10
5:00 pm - TBD
⭐🟩🚍⚽👦🏽AWAY VARSITY BOYS SOCCER PAWLING @ Arlingtonfrom 5:00 pm to 7:00 pm
Location: Arlington High School

Thursday,  September  10
5:00 pm - 7:00 pm
(NOTE: Game will start at 6PM) 🟥🚑👮🏽🏈HOME (LEAGUE) ⭐⭐⭐⭐⭐HOME OPENER⭐⭐⭐⭐⭐FB V PAWLING HIGH SCHOOL vs. Eldred HSfrom 6:00 pm to 9:00 pm
Location: Pawling Tiger Stadium at PCMS

Thursday,  September  10
6:00 pm - 9:00 pm
⭐🟩🚍AWAY JV VOLLEYBALL PAWLING @ Haldane HSfrom 6:30 pm to 8:00 pm
Location: Haldane High School

Thursday,  September  10
6:30 pm - 8:00 pm
⭐🟩🚍🏑AWAY VARSITY FIELD HOCKEY PAWLING @ Hendrick Hudson HSfrom 7:00 pm to 9:00 pm
Location: Hendrick Hudson High School

Thursday,  September  10
7:00 pm - 9:00 pm
Friday September 11 2026
🏈🏈🏈First MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Friday,  September  11
3:00 pm - 5:00 pm
🎾SKILLS VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:30 pm to 4:30 pm
Location: BREWSTER HIGH

Friday,  September  11
3:30 pm - 4:30 pm
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Friday,  September  11
5:00 pm - 8:00 pm
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Friday,  September  11
6:00 pm - 8:00 pm
Rosh Hashanah starts at Sundown 7:11 PMfrom 7:10 pm to TBD
Location: Pawling HS

Friday,  September  11
7:10 pm - TBD
Saturday September 12 2026
⭐🟩🚍🏃🏽‍♂️🏃🏽‍♀️AWAY VARSITY CROSS COUNTRY PAWLING @ MOUNT ACADEMY INVITE (7:30 am bus)from 9:30 am to TBD
Location: The Mount Academy

Saturday,  September  12
9:30 am - TBD
Rosh Hashanah ends at Sundown 7:09 PMfrom 7:10 pm to TBD
Location: Pawling HS

Saturday,  September  12
7:10 pm - TBD
13 14 15 16 17 18 19
Sunday September 13 2026
 
Monday September 14 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Monday,  September  14
3:00 pm - 5:00 pm
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Monday,  September  14
3:15 pm - 5:00 pm
⭐🟥⚽👦🏽HOME VARSITY BOYS SOCCER PAWLING V. Putnam Valley HSfrom 5:00 pm to 7:00 pm
Location: Pawling Tiger Stadium at PCMS

Monday,  September  14
5:00 pm - 7:00 pm
⭐🟥🏐🏐HOME JV VOLLEYBALL PAWLING VS Keio Academyfrom 5:00 pm to TBD
Location: Pawling HS

Monday,  September  14
5:00 pm - TBD
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Monday,  September  14
6:00 pm - 8:00 pm
⭐🟥🏐HOME VARSITY VOLLEYBALL PAWLING VS Keio Academyfrom 6:45 pm to TBD
Location: Pawling HS

Monday,  September  14
6:45 pm - TBD
Tuesday September 15 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Tuesday,  September  15
3:00 pm - 5:00 pm
⭐🟩🚍🎾AWAY VARSITY GIRLS TENNIS BREWSTER/PAWLING VS CARMEL HIGH SCHOOLfrom 4:00 pm to TBD
Location: Brewster High School

Tuesday,  September  15
4:00 pm - TBD
⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ Greenburgh North Castle/Clark Academy HSfrom 4:30 pm to 6:00 pm
Location: Greenburgh-North Castle UFSD

Tuesday,  September  15
4:30 pm - 6:00 pm
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  15
5:00 pm - 8:00 pm
⭐🟩🚍⚽⚽👦🏽AWAY JV BOYS SOCCER PAWLING @ PUTNAM VALLEYfrom 5:00 pm to TBD
Location: Putnam Valley High School

Tuesday,  September  15
5:00 pm - TBD
⭐🟩🚍🏐🏐AWAY JV VOLLEYBALL PAWLING @ Geenburgh North Castle/Clark Academyfrom 6:15 pm to 7:45 pm
Location: Greenburgh-North Castle UFSD

Tuesday,  September  15
6:15 pm - 7:45 pm
Wednesday September 16 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Wednesday,  September  16
3:00 pm - 5:00 pm
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Wednesday,  September  16
3:15 pm - 5:00 pm
⭐🟩🚍⚽👦🏽(Bus at 2:30 PM early dismissal for team at 2:15 PM)AWAY VARSITY BOYS SOCCER PAWLING @ Spring Valley HSfrom 5:00 pm to 7:00 pm
Location: Spring Valley High School

Wednesday,  September  16
5:00 pm - 7:00 pm
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Wednesday,  September  16
6:00 pm - 8:00 pm
Thursday September 17 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Thursday,  September  17
3:00 pm - 5:00 pm
🎾 VARSITY GIRLS TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Thursday,  September  17
3:15 pm - 5:00 pm
(NOTE: This game will NOT be rescheduled)⭐🟥🏐🏐HOME JV VOLLEYBALL PAWLING VS Scarsdale HSfrom 4:30 pm to TBD
Cancelled   Cancelled

Location: Pawling HS

Thursday,  September  17
4:30 pm - TBD
⭐🟩🚍⚽👧🏽AWAY VARSITY GIRLS SOCCER PAWLING @ LINCOLN OBAMAfrom 4:30 pm to TBD
Location: Lincoln High School

Thursday,  September  17
4:30 pm - TBD
⭐🟩🚍🎾AWAY VARSITY TENNIS BREWSTER/PAWLING @ JJEF (Taconic Sport and Racquet)from 4:30 pm to TBD
Location: Taconic Sport & Racquet

Thursday,  September  17
4:30 pm - TBD
⭐🟩🚍🏃🏽‍♂️🏃🏽‍♀️AWAY VARSITY CROSS COUNTRY PAWLING @ WOODLANDS HIGH SCHOOL (early dismissal - 2:40 pm bus)from 4:30 pm to TBD
Location: Woodlands HS Field

Thursday,  September  17
4:30 pm - TBD
⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ North Salem HSfrom 4:30 pm to 6:00 pm
Location: Haldane High School

Thursday,  September  17
4:30 pm - 6:00 pm
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Thursday,  September  17
5:00 pm - 8:00 pm
⭐🟩🚍🏐🏐AWAY JV VOLLEYBALL PAWLING @ North Salem HSfrom 6:15 pm to 8:00 pm
Location: Haldane High School

Thursday,  September  17
6:15 pm - 8:00 pm
(NOTE: This game will NOT be rescheduled)⭐🟥🏐HOME VARSITY VOLLEYBALL PAWLING VS Scarsdale HSfrom 6:30 pm to TBD
Cancelled   Cancelled

Location: Pawling HS

Thursday,  September  17
6:30 pm - TBD
Friday September 18 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Friday,  September  18
3:00 pm - 5:00 pm
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Friday,  September  18
3:15 pm - 5:00 pm
⭐🟩🚍🏑AWAY VARSITY FIELD HOCKEY PAWLING @ MAHOPAC HS STADIUMfrom 4:30 pm to TBD
Location: Mahopac High School

Friday,  September  18
4:30 pm - TBD
⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ Riverside HSfrom 4:45 pm to 6:15 pm
Location: Riverside HS (Yonkers)

Friday,  September  18
4:45 pm - 6:15 pm
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Friday,  September  18
5:00 pm - 8:00 pm
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Friday,  September  18
6:00 pm - 8:00 pm
🟩🏈🚍🚍 (LEAGUE) AWAY FB V PAWLING HIGH SCHOOL @ Sullivan West HSfrom 7:00 pm to 10:00 pm
Location: Sullivan West HS

Friday,  September  18
7:00 pm - 10:00 pm
Saturday September 19 2026
VARSITY CROSS COUNTRY 🟥⭐🏃‍♂️🚑Dan Purdy Cross Country Invitationalfrom 8:30 am to 1:30 pm
Location: Pawling HS Grass Field

Saturday,  September  19
8:30 am - 1:30 pm
⭐🟥🚍🎾HOME VARSITY GIRLS TENNIS BREWSTER/PAWLING VS MAHOPAC HIGH SCHOOLfrom 11:00 am to TBD
Location: Brewster High School

Saturday,  September  19
11:00 am - TBD
⭐🟩🚍🏐🏐AWAY JV VOLLEYBALL PAWLING @ Briarcliff HSfrom 12:45 pm to 2:15 pm
Location: Briarcliff High School

Saturday,  September  19
12:45 pm - 2:15 pm
20 21 22 23 24 25 26
Sunday September 20 2026
 
Monday September 21 2026
❌❌❌❌❌❌❌❌❌❌YOM KIPPUR (NO SCHOOL 0N 9/21/26 FOR PAWLING CSD) TBD
Location: Pawling HS

Monday,  September  21
TBD
Tuesday September 22 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Tuesday,  September  22
3:00 pm - 5:00 pm
⭐🟥🏃🏽‍♂️🏃🏽‍♀️🏃🏽‍♂️🏃🏽‍♀️🏃🏽‍♂️🏃🏽‍♀️HOME MODIFIED CROSS COUNTRY VS CARMEL, VAN WYCK MSfrom 4:30 pm to TBD
Location: Pawling High School

Tuesday,  September  22
4:30 pm - TBD
⭐🟩🚍🏃🏽‍♂️🏃🏽‍♀️AWAY VARSITY CROSS COUNTRY PAWLING @ NORTH SALEM HIGH SCHOOLfrom 4:30 pm to TBD
Location: North Salem High School Middle School

Tuesday,  September  22
4:30 pm - TBD
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  22
5:00 pm - 8:00 pm
⭐🟥⚽👦🏽HOME VARSITY BOYS SOCCER PAWLING V. Tuckahoefrom 5:00 pm to 7:00 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  22
5:00 pm - 7:00 pm
⭐🟩🚍🎾AWAY VARISTY GIRLS TENNIS BREWSTER/PAWLING @ ARLINGTON HIGH SCHOOLfrom 5:00 pm to TBD
Location: Arlington High School

Tuesday,  September  22
5:00 pm - TBD
⭐🟩🏑AWAY VARSITY FIELD HOCKEY PAWLING @ CARMEL (TURF FIELD)from 6:30 pm to TBD
Location: Carmel High School

Tuesday,  September  22
6:30 pm - TBD
BOE MEETING 7PMfrom 7:00 pm to TBD
Location: Pawling MS

Tuesday,  September  22
7:00 pm - TBD
Wednesday September 23 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Wednesday,  September  23
3:00 pm - 5:00 pm
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Wednesday,  September  23
3:15 pm - 5:00 pm
⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ Croton HSfrom 4:30 pm to 6:00 pm
Location: Croton-Harmon

Wednesday,  September  23
4:30 pm - 6:00 pm
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Wednesday,  September  23
5:00 pm - 8:00 pm
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Wednesday,  September  23
6:00 pm - 8:00 pm
⭐🟩🚍🏐🏐AWAY JV VOLLEYBALL PAWLING @ Croton HSfrom 6:15 pm to 7:45 pm
Location: Croton - Harmon High School

Wednesday,  September  23
6:15 pm - 7:45 pm
Thursday September 24 2026
⭐🟥🚍🎾HOME VARSITY GIRLS TENNIS BREWSTER/PAWLING VS ROY C KETCHAM HIGH SCHOOLfrom 4:30 pm to TBD
Location: Roy C Ketcham Senior High School

Thursday,  September  24
4:30 pm - TBD
⭐🟩🚍🏑AWAY VARSITY FIELD HOCKEY PAWLING @ PUTNAM VALLEY HSfrom 4:30 pm to TBD
Location: Putnam Valley High School

Thursday,  September  24
4:30 pm - TBD
Moved to 9/25(Changed to a Home scrimmage due to conflict at Haldane)⭐🟥🏈🏈🏈Home MODIFIED FOOTBALL PAWLING AT Haldane HSfrom 5:00 pm to 7:15 pm
Cancelled   Cancelled

Location: Pawling HS Grass Field

Thursday,  September  24
5:00 pm - 7:15 pm
⭐🟥⚽👦🏽HOME VARSITY BOYS SOCCER PAWLING V. Briarcliff HSfrom 5:00 pm to 7:00 pm
Location: Pawling Tiger Stadium at PCMS

Thursday,  September  24
5:00 pm - 7:00 pm
⭐🟩🚍⚽⚽👦🏽AWAY JV BOYS SOCCER PAWLING @ BRIARCLIFF HSfrom 5:00 pm to TBD
Location: Briarcliff High School

Thursday,  September  24
5:00 pm - TBD
Friday September 25 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Friday,  September  25
3:00 pm - 5:00 pm
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Friday,  September  25
3:15 pm - 5:00 pm
⭐🟩🚍🏑🏑🏑AWAY MODIFIED FIELD HOCKEY PAWLING @ Yorktown HSfrom 4:30 pm to 6:30 pm
Location: Yorktown High School

Friday,  September  25
4:30 pm - 6:30 pm
Moved to 9/25(Changed to a Home scrimmage due to conflict at Haldane)⭐🟥🏈🏈🏈Home MODIFIED FOOTBALL PAWLING vs. Haldane HSfrom 5:00 pm to 7:15 pm
Location: Pawling Tiger Stadium at PCMS

Friday,  September  25
5:00 pm - 7:15 pm
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Friday,  September  25
5:00 pm - 8:00 pm
⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ Westlake HSfrom 5:30 pm to 7:00 pm
Location: Westlake High School

Friday,  September  25
5:30 pm - 7:00 pm
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Friday,  September  25
6:00 pm - 8:00 pm
Show MenuClick this to show the menu.🟥🚑👮🏽🏈HOME(LEAGUE) FB V PAWLING HIGH SCHOOL vs. Corinth HSfrom 7:00 pm to 10:00 pm
Cancelled   Cancelled

Location: Pawling Tiger Stadium at PCMS

Friday,  September  25
7:00 pm - 10:00 pm
⭐🟩🚍🏐🏐AWAY JV VOLLEYBALL PAWLING @ Westlake HSfrom 7:15 pm to 8:45 pm
Location: Westlake High School

Friday,  September  25
7:15 pm - 8:45 pm
Saturday September 26 2026
⭐🟩🚍🏃🏽‍♂️🏃🏽‍♀️AWAY VARSITY CROSS COUNTRY PAWLING @ ADMIRAL HARRIER INVITE (Hudson Valley Sports Dome)from 8:30 am to TBD
Location: Hudson Valley Sportsdome

Saturday,  September  26
8:30 am - TBD
⭐🟥⚽⚽👦🏽HOME JV BOYS SOCCER PAWLING VS CROTON HARMONfrom 11:00 am to TBD
Location: Pawling HS Grass Field

Saturday,  September  26
11:00 am - TBD
⭐🟩🚍⚽👦🏽AWAY VARSITY BOYS SOCCER PAWLING @ Croton HSfrom 11:00 am to 1:00 pm
Location: Croton-Harmon Senior High School

Saturday,  September  26
11:00 am - 1:00 pm
⭐🟩🚍🎾AWAY VARSITY GIRLS TENNIS BREWSTER/PAWLING @ CARMEL HIGH SCHOOLfrom 11:00 am to TBD
Location: Carmel High School

Saturday,  September  26
11:00 am - TBD
🟥🚑👮🏽🏈HOME(LEAGUE) 👕👕👕(Shirt Off My Back Game)FB V PAWLING HIGH SCHOOL vs. Corinth HSfrom 1:00 pm to 4:00 pm
Location: Pawling Tiger Stadium at PCMS

Saturday,  September  26
1:00 pm - 4:00 pm
27 28 29 30 1 2 3
Sunday September 27 2026
 
Monday September 28 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Monday,  September  28
3:00 pm - 5:00 pm
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Monday,  September  28
3:15 pm - 5:00 pm
⭐🟩🏃🏽‍♂️🏃🏽‍♀️🏃🏽‍♂️🏃🏽‍♀️🏃🏽‍♂️🏃🏽‍♀️AWAY MODIFIED CROSS COUNTRY PAWLING @ UNIONVALE MIDDLE SCHOOLfrom 4:30 pm to 5:30 pm
Location: Union Vale Middle School

Monday,  September  28
4:30 pm - 5:30 pm
⭐🟥⚽⚽👦🏽HOME JV BOYS SOCCER PAWLING VS PLEASANTVILLEfrom 5:00 pm to TBD
Location: Pawling Tiger Stadium at PCMS

Monday,  September  28
5:00 pm - TBD
⭐🟩🚍⚽👦🏽AWAY VARSITY BOYS SOCCER PAWLING @ Pleasantville HSfrom 5:00 pm to 7:00 pm
Location: Pleasantville High School

Monday,  September  28
5:00 pm - 7:00 pm
⭐🟩🚍🏑AWAY VARSITY FIELD HOCKEY PAWLING @ IRVINGTON HS - MESZAROS FIELDfrom 5:00 pm to 7:00 pm
Location: Irvington High School

Monday,  September  28
5:00 pm - 7:00 pm
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Monday,  September  28
6:00 pm - 8:00 pm
Tuesday September 29 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Tuesday,  September  29
3:00 pm - 5:00 pm
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Tuesday,  September  29
3:15 pm - 5:00 pm
⭐🟥🏐🏐HOME JV VOLLEYBALL PAWLING VS Hastings HSfrom 4:30 pm to TBD
Location: Pawling HS

Tuesday,  September  29
4:30 pm - TBD
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  29
5:00 pm - 8:00 pm
⭐🟥⚽👧🏽HOME VARSITY GIRLS SOCCER PAWLING VS RAMAPOfrom 5:00 pm to TBD
Location: Pawling Tiger Stadium at PCMS

Tuesday,  September  29
5:00 pm - TBD
⭐🟥🚍🎾HOME VARSITY GIRLS TENNIS PAWLING/BREWSTER VS JJEF HIGH SCHOOLfrom 5:00 pm to TBD
Location: Brewster High School

Tuesday,  September  29
5:00 pm - TBD
⭐🟩🚍⚽⚽⚽👦🏽👦🏻👦🏻AWAY MODIFIED BOYS SOCCER PAWLING V. Brewster @ North Salemfrom 5:00 pm to 7:00 pm
Location: North Salem High School Middle School

Tuesday,  September  29
5:00 pm - 7:00 pm
⭐🟥🏐HOME VARSITY VOLLEYBALL PAWLING VS Hastings HSfrom 6:15 pm to TBD
Location: Pawling HS

Tuesday,  September  29
6:15 pm - TBD
Wednesday September 30 2026
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Wednesday,  September  30
3:00 pm - 5:00 pm
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Wednesday,  September  30
3:15 pm - 5:00 pm
(4:45/5:00) PM start followed by Boys Varsity Soccer at 7PM)⭐🟥🏑HOME VARSITY FIELD HOCKEY PAWLING VS NORTH SALEMfrom 4:45 pm to TBD
Location: Pawling Tiger Stadium at PCMS

Wednesday,  September  30
4:45 pm - TBD
⭐🟩🚍⚽⚽👦🏽AWAY JV BOYS SOCCER PAWLING @ NORTH SALEMfrom 5:00 pm to TBD
Location: North Salem High School Middle School

Wednesday,  September  30
5:00 pm - TBD
⭐🟩🚍👧🏽⚽⚽⚽AWAY MODIFIED GIRLS SOCCER PAWLING @ NORTH SALEM (BREWSTER HIGH SCHOOL)from 5:00 pm to TBD
Location: Brewster High School

Wednesday,  September  30
5:00 pm - TBD
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Wednesday,  September  30
6:00 pm - 8:00 pm
(7 PM start after Field Hockey at 5 PM)⭐🟥⚽👦🏽HOME VARSITY BOYS SOCCER PAWLING V. North Salem HSfrom 7:00 pm to 9:00 pm
Location: Pawling Tiger Stadium at PCMS

Wednesday,  September  30
7:00 pm - 9:00 pm
Thursday October 1 2026
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Thursday,  October  1
3:15 pm - 5:00 pm
🟥🏈🏈🏈HOME MODIFIED FOOTBALL PAWLING V. Dover HSfrom 4:15 pm to 6:30 pm
Location: Pawling Tiger Stadium at PCMS

Thursday,  October  1
4:15 pm - 6:30 pm
⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ Irvington HSfrom 4:30 pm to 6:00 pm
Location: Irvington High School

Thursday,  October  1
4:30 pm - 6:00 pm
⚽👦🏽VARSITY/JV BOYS SOCCER PRACTICE 5:00-8:00 PMfrom 5:00 pm to 8:00 pm
Location: Pawling Tiger Stadium at PCMS

Thursday,  October  1
5:00 pm - 8:00 pm
⭐🟥🏑HOME VARSITY FIELD HOCKEY PAWLING VS HASTINGSfrom 5:00 pm to TBD
Location: Pawling Tiger Stadium at PCMS

Thursday,  October  1
5:00 pm - TBD
⭐🟩🚍⚽👧🏽AWAY VARSITY GIRLS SOCCER PAWLING @ SPRING VALLEYfrom 5:00 pm to TBD
Location: Spring Valley High School

Thursday,  October  1
5:00 pm - TBD
⭐🟩🚍🎾AWAY VARSITY GIRLS TENNIS BREWSTER/PAWLING VS MAHOPAC HIGH SCHOOLfrom 5:00 pm to TBD
Location: Mahopac High School

Thursday,  October  1
5:00 pm - TBD
⭐🟩🚍🏐🏐AWAY JV VOLLEYBALL PAWLING @ Irvington HSfrom 6:15 pm to 7:45 pm
Location: Irvington High School

Thursday,  October  1
6:15 pm - 7:45 pm
Friday October 2 2026
EARLY DISMISSAL AND EVACUATION DRILLfrom 2:15 pm to 2:40 pm
Location: Pawling HS

Friday,  October  2
2:15 pm - 2:40 pm
🏈🏈🏈MODIFIED FOOTBALL PRACTICEfrom 3:00 pm to 5:00 pm
Location: Pawling HS Grass Field

Friday,  October  2
3:00 pm - 5:00 pm
🎾 VARSITY TENNIS @ BREWSTER HIGH SCHOOLfrom 3:15 pm to 5:00 pm
Location: Brewster High School

Friday,  October  2
3:15 pm - 5:00 pm
⭐⭐⭐⭐⭐ SENIOR GAME⭐⭐⭐⭐⭐🟥⚽👦🏽HOME VARSITY BOYS SOCCER PAWLING V. Haldane HSfrom 5:00 pm to 7:00 pm
Location: Pawling Tiger Stadium at PCMS

Friday,  October  2
5:00 pm - 7:00 pm
⭐🟩🚍⚽⚽👦🏽AWAY JV BOYS SOCCER PAWLING @ HALDANEfrom 5:00 pm to TBD
Location: Haldane High School

Friday,  October  2
5:00 pm - TBD
🏀🏀🏀🏀🏀 PD BOYS AAU Basketball w/ S.M. at TBAfrom 6:00 pm to 8:00 pm
Location: TBA

Friday,  October  2
6:00 pm - 8:00 pm
⭐🟩🚍🏐AWAY VARSITY VOLLEYBALL PAWLING @ Keio Academyfrom 6:30 pm to 8:00 pm
Location: Keio Academy

Friday,  October  2
6:30 pm - 8:00 pm
🟩🏈🚍🚍 (LEAGUE) AWAY FB V PAWLING HIGH SCHOOL @ Pine Plains/Rhinebeck HS HSfrom 7:00 pm to 10:00 pm
Location: Pine Plains Central School District

Friday,  October  2
7:00 pm - 10:00 pm
⭐🟩🚍🏐🏐AWAY JV VOLLEYBALL PAWLING @ Keio Academy HSfrom 8:15 pm to 9:45 pm
Location: Keio Academy

Friday,  October  2
8:15 pm - 9:45 pm
Saturday October 3 2026
⭐🟥⚽👧🏽HOME VARSITY GIRLS SOCCER PAWLING VS HALDANEfrom 2:00 pm to TBD
Location: Pawling Tiger Stadium at PCMS

Saturday,  October  3
2:00 pm - TBD