| Sport | Date | Teams | Location | Time |
| Boys Cross Country | Oct 24 | Mount Greylock at Monument Mountain | | 09:00 AM |
| Boys Cross Country | Oct 24 | Wahconah at Mount Everett | | 11:00 AM |
| co-ed Golf | Oct 24 | Multiple teams at Berkshire County Championship | Wyantenuck | 02:00 PM |
| Girls Cross Country | Oct 24 | Wahconah at Mount Everett | | 09:00 AM |
| Girls Cross Country | Oct 24 | Mount Greylock at Monument Mountain | | 11:55 AM |
| |
| Boys Cross Country | Oct 31 | Wahconah at Monument Mountain | | 09:00 AM |
| Boys Cross Country | Oct 31 | Mount Everett at Mount Greylock | | 11:30 AM |
| Girls Cross Country | Oct 31 | Wahconah at Monument Mountain | | 11:30 AM |
| Girls Cross Country | Oct 31 | Mount Everett at Mount Greylock | | 11:30 AM |
| |
| Boys Cross Country | Nov 07 | Monument Mountain at Mount Everett | | 09:00 AM |
| Boys Cross Country | Nov 07 | Mount Greylock at Wahconah | | 11:55 AM |
| Girls Cross Country | Nov 07 | Mount Greylock at Wahconah | | 09:00 AM |
| Girls Cross Country | Nov 07 | Monument Mountain at Mount Everett | | 11:00 AM |
| |
| Boys Cross Country | Nov 14 | Multiple teams at Mount Greylock | Time TBA | 12:00 AM |
| Girls Cross Country | Nov 14 | Multiple teams at Mount Greylock | Time TBA | 12:00 PM |
