| 2021 Registration Opens | Monday, January 4 | Registration for Spring Baseball & Softball opens at ossiningjcysll.com |
| Winter Instructional Sessions Begin | TBD | Ossining Recreation Center Gym - Dates & Times TBA. Will be rotated by divisions including Tee Ball, Minors, Intermediate, Little League & Softball |
| In Person Registration | TBD | Ossining Recreation Center |
| Last Day for Discounted Registration | Sunday, March 14 | Registration increases $25 as of March 15th |
| Majors/Intermediate & Majors/Little League Assessments | Saturday, April 10 | In an increase in COVID-19 safety precautions, 2021 assessments will be held outdoors at Ryder Park.
All Majors/Intermediate (9-10) & Majors/Little League (11-12) players must attend (1) session. Player dates and times TBA. |
| Majors/Intermediate & Majors/Little League Assessments | Sunday, April 11 | In an increase in COVID-19 safety precautions, 2021 assessments will be held outdoors at Ryder Park.
All Majors/Intermediate (9-10) & Majors/Little League (11-12) players must attend (1) session. Player dates and times TBA. |
| All Coaches Meeting & Training | Saturday, April 10 | Please save this date for a 3 hour meeting on safety, skills and coaching resources. For added COVID safety precautions, the 2021 meeting will held be outdoors, at the Ryder Park Pavilion. |
| 2021 JCYS Rosters & Schedule Announcement | Monday, April 12 | Rosters and schedules for all divisions to be announced on or before April 12th. |
| First Day Of On Field Practices | Monday, April 12 | On-field practices begin for all Baseball and Softball divisions. |
| 2021 Opening Day | Saturday, April 17 | Tee Ball, Minors Baseball and all Softball divisions to open on April 17th. Due to increased safety precautions and limiting group sizes, there will be no Opening Day parade. |
| Ossining Travel Baseball Tryouts | Saturday, April 17 | Annual tryouts for Ossining Travel Baseball teams. Tryouts for 8U, 9U at Ryder Park, tryouts for 11U & 12U at Nelson Park. Specific team dates & times TBA. |
| Ossining Travel Baseball Tryouts | Sunday, April 18 | Annual tryouts for Ossining Travel Baseball teams. Tryouts for 8U, 9U at Ryder Park, tryouts for 11U & 12U at Nelson Park. Specific team dates & times TBA. |
| Majors/Intermediate Umpire Training | Sunday, April 18 | Please save this date for an on field umpire training at Ryder Park. If interested in umpiring Majors/Intermediate games for the 2021 season please contact Dave Capasso at [email protected] |
| Picture Day - All Divisions | Saturday, May 15 | Veterans Park (Majors/Intermediate, Majors/Little League & All Softball) & Roosevelt School Fields (Tee Ball & Minors) |
| Majors/Little League Division Championship | Saturday, June 12 | Ryder Park, 10:00am |
| Majors/Intermediate All-Star Game | Saturday, June 19 | Veterans Park (Lower Field) |