| Date | Mileage | Loops |
| 12/15 | 10.0 | Southern Trail |
| 12/22 | 11.0 | Revised Old Mill |
| 12/29 | 13.0 | Lakefront Bridge + Old Elm |
| 1/5 | 8.0 | Lake Bluff |
| 1/12 | 14.3 | Lake Bluff + Lakefront |
| 1/19 | 15.0 | Revised Old Mill + College |
| 1/26 | 16.3 | Southern Trail + Lakefront |
| 2/2 | 13.0 | Lakefront Bridge + Old Elm or Barrington |
| 2/9 | 17.5 | Military Loop |
| 2/16 | 18.0 | Southern Trail + Lake Bluff |
| 2/23 | 19.0 | Revised Old Mill + Lake Bluff |
| 3/1 | 13.0 | Lake Front Bridge + Old Elm or Barrington |
| 3/8 | 20.0 | Lakefront Bridge + Southern Trail |
| 3/16 | 13.1 | Cary March Madness Half |
| 3/22 | 20.3 | Souther Trail + Lakefront + College |
| 3/29 | 13.0 | Lakefront Bridge + Old Elm or Barrington |
| 4/5 | 20.9 | Big Kahuna |
| 4/12 | 8.0 | Lake Bluff |
| 4/20-4/21 | 26.2 | Equestrian Connection or Boston |