| Registration Opens | July 1 |
| Early Bird Deadline | July 10 |
| Registration Closes | August 9 |
| Coaches Meeting | August 7 |
| Skills Day (Little League) | August 10 |
| Skills Day (Juniors/Seniors) & Babe Ruth 18U Baseball Tryouts | August 11 (afternoon) |
| Challenge Baseball Tryouts | August 11 (afternoon) |
| Team Drafts | August 15-18 |
| Team Announcements | week of August 19th |
| Practices Begin | week of August 26th |
| Labor Day Break* | August 30 - September 2* |
| Games Begin | September 5-10 |
| Pictures | September 25-28 |
| Halloween Break* | October 31* |
| Season Ends | by November 2 |
* No scheduled league activities during breaks.