| Upcoming Events | Date & Time |
| First Day of HS Fall Sports Practices Cross Country, Field Hockey, Soccer, Tennis, Volleyball (Football begins on Tuesday August 18 - re: Section 9 (8-Man Football)) | Mon 08/24/2026 (All Day) |
| ⭐🏃🏼♂️🏃🏼♀️⚾🥎🏌🏼♂️🥍🩰⭐Pawling High School Spring Sports Awards⭐ | Thu 06/17/2027 6:30 pm - 9:30 pm |