| JCYS Annual Membership Meeting | Wednesday, January 5 | 7:30pm at the Ossining Community Center. Annual JCYS membership meeting to review the state of the league and elect the 2022 Board of Directors. This meeting is open to all JCYS members. |
| 2022 Registration Opens | Friday, January 7 | Registration for Spring Baseball & Softball opens at ossiningjcysll.com |
| Winter Instructional Sessions Begin | TBD January | Ossining Community Center Gym - Dates & Times TBA. Will be rotated by divisions including Tee Ball, Minors, Intermediate, Little League & Softball |
| In Person Registration | TBD January | Ossining Community Center |
| In Person Registration | TBD February | Register in person at the Ossining Community Center |
| In Person Registration | TBD March | Register in person at the Ossining Community Center |
| Last Day for Discounted Registration | Sunday, March 20 | Registration increases $25 as of March 20th |
| 2022 Registration Closes | Friday, April 1 | Registration for all divisions with the exception of Senior Baseball will close |
| Intermediate & Majors Baseball Assessments | Saturday, April 2 | All Intermediate (9-10) & Majors (11-12) players must attend (1) session. Player dates and times TBA. |
| All Coaches Meeting & Training | Sunday April 3 | Please save this date for a 3 hour meeting on safety, skills and coaching resources. |
| Intermediate Umpire Training | Sunday, April 4 | Please save this date for an on-field umpire training at Ryder Park. If interested in umpiring Intermediate games for the 2022 season please contact David Capasso at [email protected] |
| 2022 JCYS Rosters & Schedule Announcement | Monday, April 4 | Rosters and schedules for all divisions to be announced on or before April 12th. |
| First Day Of On Field Practices | Monday, April 4 | On-field practices begin for all Baseball and Softball divisions. |
| 2022 Opening Day | Saturday, April 9 | Information on Opening Day games, parade and on-field ceremonies, TBA. |
| Ossining Travel Baseball Tryouts | Sunday, May 8 | Annual tryouts for Ossining Travel Baseball teams. Our hope is to field teams in 8U, 9U, 10U, 12U in 2022. Specific team dates & times TBA. |
| Picture Day - All Divisions | Saturday, May 14 | Veterans Park (Majors/Intermediate, Majors/Little League & All Softball) & Roosevelt School Fields (Tee Ball & Minors) |
| Majors Division Championship Game | Saturday, June 11 | Ryder Park, 10:00am |
| Intermediate All-Star Game | Saturday, June 25 | Veterans Park (Lower Field) |