| Fri, Sep 9 | Taconic, Mt. Everett, Drury, Hoosac @ Monument Mt. | Monument Mountain | Great Barrington, MA | | | |
| Wed, Sep 14 | Taconic, Drury, BART, Hoosac @ Wahconah (HS) | Wahconah Regional HS | Dalton, MA | 4:30 PM | | |
| Wed, Sep 21 | Taconic, Monument, Pittsfield, Drury, Everett @ Mt. Greylock | Mount Greylock Regional HS | Williamstown, MA | 4:30 PM | | |
| Sat, Sep 24 | Amherst Invitational | Hampshire College XC course | Amherst, MA | 12:00 AM | | |
| Tue, Sep 27 | Taconic vs. Mt. Greylock, Lenox, Hoosac, Pittsfield | Taconic High School | Pittsfield, MA | 4:30 PM | | |
| Wed, Oct 5 | Taconic, Hoosac, St. Joe, Lenox @ Mount Everett | Mount Everett Regional High School | Sheffield, MA | 4:30 PM | | |
| Tue, Oct 11 | Taconic, Hoosac, Lenox, Mt. Greylock @ Pittsfield | Reid Middle School | Pittsfield, MA | 4:30 PM | | |
| Sat, Oct 15 | Brown Invitational | Goddard Memorial State Park | Warwick, RI | 9:20 AM | | |
| Wed, Oct 19 | Taconic, Wahconah, Hoosac, Bart, Mt. Everett @ Mt. Greylock | Mount Greylock Regional HS | Williamstown, MA | 4:30 PM | | |
| Sat, Oct 29 | Berkshire County Cross Country Championships | Berkshire CC XC Course | Pittsfield, MA | 1:00 PM | | |
| Sat, Nov 12 | Western MA XC Champs | Northfield Mountain | Northfield, MA | | | |
