| KPW Early Signup for Bruins LTP | July 31st |
| USA Hockey Registrations due to Team Managers | Early Aug |
| 18u Teams Begin | Late Aug |
| Coaches Meeting/Uniforms (6pm @ Conrads) | Aug 29th |
| All KPW Travel Teams begin practicing | Sept 1st |
| SSC Coaches Meeting (U10-U19) | Early Sept |
| SSC Checking Clinic for new 14U players | Sept 6th or 7th |
| Driscoll Skating Skills Program Begins | Sept 6th |
| Stop It Goalie Skills Starts | Sept |
| SSC Mite Coaches Meeting (U6 & U8 ONLY | Sept |
| Conference Games Begin | Mid Sept |
| Bruins Learn to Play (Starts) | Oct 5th |
| Mass Hockey District 5 Playdown Process Starts | Mid Oct |
| SSC Parity Change Request | 20-Oct |
| Instructional Program Begins | 25-Oct |
| Mite Development Starts | 25-Oct |
| SSC Final Divisions (Parity Changes made) | 14-Nov |
| 18 Half Season Ends | Nov 30th |
| SSC Conference Parody Reset | Nov 15th |
| Deadline to Finish Coach Certification | Early Dec |
| KPW runs "Play Hockey for Free Day" | Feb (TBD) |
| Coaches Complete Player Evaluations | Late Feb |
| Regular Season ends (Conference) | March 16th |
| Conference Playoffs | End of March |
| Tryouts held for Next Season (Allowed) | Mid March |
| MA State Tournament Playoffs Boys | Late March |
| MA State Tournament Playoffs Girls | Late March |
| Season Ends/Formal Team activities over | Early April |
| Payments due to allow for Placement to KPW | Mid April |
| Teams Formed and Announced (next season) | Late April |
| Uniform Fitting and Custom Gear Orders | Last week of April |
| Spring Offseason (Open Skates/Scrimms) | May/June |
| Summer Open Ice (4 sheets) | July/Aug |
| Wrist Curls / Puck Shooting / Hockey Conditioning | Year Round |