| Date | Boston | Equestrian / Kenosha | Loops |
| Dec 13th | 8.0 | 8.0 | Military Out and Back |
| Dec 20th | 10.0 | 8.0 | Lakefront Bridge / Lake Bluff Loop |
| Dec 27th | 10.0 | 10.0 | Southern Trail |
| Jan 3rd | 11.0 | 11.0 | Revised Old Mill |
| Jan 10th | 8.0 | 8.0 | Lake Bluff Loop |
| Jan 17th | 13.0 | 13.0 | Lakefront Bridge plus Old Elm Extension or Barrington |
| Jan 24th | 14.0 | 14.0 | Southern Trail plus College |
| Jan 31st | 10.0 | 10.0 | Lakefront Bridge |
| Feb 7th | 16.0 | 14.0 | Southern Trail plus Lakefront Loop / Southern Trail plus College |
| Feb 14th | 17.0 | 15.0 | Military Loop / Military Loop less 2 miles (turn right on Mayflower after beach) |
| Feb 21st | 13.0 | 10.0 | Lakefront Bridge plus Old Elm extension / Lakefront Bridge or Barrington |
| Feb 28th | 19.0 | 16.0 | Southern Trail plus Lake Bluff plus 1 mile / Southern Trail plus Lake Bluff (return to train station on Woodland) |
| Mar 7th | 20.0 | 17.0 | Revised Old Mill plus Lake Bluff plus 1 mile / Revised Old Mill plus Lake Bluff (return to train station on Woodland) |
| Mar 14th | 10.0 | 10.0 | Lakefront loop plus College |
| Mar 21st | 20.0 | 18.0 | Southern Trail plus Lakefront Bridge / Southern Trail plus Lake Bluff |
| Mar 28th | 13.0 | 13.0 | Lakefront Bridge plus Old Elm Extension or Barrington |
| Apr 4th | 20.0 | 20.0 | Southern Trail plus Lakefront plus College |
| Apr 11th | 10.0 | 13.0 | Lakefront Bridge / Lakefront Bridge plus Old Elm Extension |
| Apr 18th | 20.0 | Southern Trail plus Lakefront Bridge or Big Kahuna (weather permitting) | |
| Apr 20th | 26.2 | Boston Marathon | |
| Apr 25th | 10.0 | Southern Trail | |
| May 2nd / 3rd | 26.2 | Equestrian and Kenosha Marathons |