| Sunday, June 18, 2023 | Fall Rec Registration Opens |
| Monday, July 31, 2023 | Cal Ripken (5U-12U) Registration Closes |
Wednesday, August 9, 2023 -
Friday, August 11, 2023 | DK Open Workouts |
| Friday, August 11, 2023 | DK Open Workouts |
| Saturday, August 12, 2023 | Cal Ripken Rec & DK Evals |
Tuesday, August 15, 2023 -
Thursday, August 17, 2023 | Cal Ripken Rec Drafts |
| Monday, August 21, 2023 | Cal Ripken Rec Practices Begin |
| Saturday, August 26, 2023 | Babe Ruth Open Workouts |
| Thursday, August 31, 2023 | Babe Ruth Registration Closes |
| Saturday, September 2, 2023 | Babe Ruth Rec & DK Evals |
| Saturday, September 9, 2023 | Babe Ruth Practices Start |
| Saturday, September 23, 2023 | Opening Day |
| Saturday, October 7, 2023 | Picture Day |
| Saturday, October 14, 2023 | Makeup Picture Day |
| Thursday, November 9, 2023 | Final Games of Rec Regular Season |
| Monday, November 13, 2023 | Rec Playoffs Begin |
| Saturday, November 18, 2023 | Rec Playoffs End |