| Distance | Course | Men's Record | Time | Year | Women's Record | Time | Year | |
| 1 | Roxbury Mile | Michael Hall | 4.42 | 2009 | Alana Levy | 5.21 | 2019 | |
| 2.3 | West Chalybes | Dylan Weissinger | 14.12 | 2016 | Katie Burns | 17.17 | 2016 | |
| 2.4 | Up Chalybes | David Hunt | 13.07 | 2012 | Alison Lind | 14.57 | 2005 | |
| 2.4 | Down Chalybes | Dylan Weissinger | 13.16 | 2016 | ||||
| 3 | Nature preserve (Alternate Start location) | Pat Dennen | 16.28 | 2016 | Emily De La Bruyere | 17.20 | 2018 | |
| 3 | Apple - Jeep - River Rd Preserve (lollipop) | Joey Nihill | 20.14 | 2019 | Alison Masopust | 23.12 | 2019 | |
| 3.05 | Hemlock out and back | Zach Anderson | 16.35 | 2016 | Alison Masopust | 19.40 | 2019 | |
| 3.52 | Up Hemlock | Jeff Sheldon | 20.23 | 2010 | ||||
| 3.52 | Down Hemlock | Hunter McIntyre | 18.55 | 2017 | ||||
| 3.57 | Down Hemlock Up Chalybes | Jeff Sheldon | 20.38 | 2013 | ||||
| 3.57 | Down Chalybes Up Hemlock | Kevin Ortega | 20.56 | 2012 | ||||
| 3.6 | Jeep Trail (Short Course) | Jeff Sheldon | 21.18 | 2015 | Alison Masopust | 23.52 | 2019 | |
| 3.7 | Down Ranney Up Chalybes | Pat Dennen | 21.23 | 2014 | ||||
| 3.7 | Down Chalybes Up Ranney Hill | Jeff Sheldon | 20.53 | 2013 | ||||
| 3.7 | Down Ranney | Jeff Sheldon | 22.04 | 2011 | ||||
| 3.7 | Up Ranney | Desmond O'Grady | 20.36 | 2010 | Alison Masopust | 23.02 | 2019 | |
| 3.9 | Jeep Trail | Jeff Sheldon | 22.26 | 2012 | ||||
| 4.2 | Down Hemlock Up Ranney | Jack Kuenzle | 24.00 | 2019 | Alison Lind | 25.50 | 2005 | |
| 4.2 | Down Ranney Up Hemlock | Taylor Phillips | 22.53 | 2014 | ||||
| 4.3 | High Bridge - counter clockwise | Desmond O'Grady | 24.11 | 2010 | Alison Masopust | 27.09 | 2019 | |
| 4.3 | Down Highbridge Reverse | Desmond O'Grady | 23.55 | 2010 | ||||
| 4.4 | Up Chalybes Down Hemlock | Jeff Sheldon | 26.21 | 2010 | Alison Masopust | 29.39 | 2018 | |
| 4.8 | Judd's Bridge road (Short Course) | Desmond O'Grady | 27.50 | 2010 | ||||
| 5 | Down Ranney Up Hemlock Down Chalybes | Ken Merrick | 29.58 | 2013 | ||||
| 5 | Up Squire rd | Craig Hunt | 29.07 | 2011 | ||||
| 5 | Down Squire rd | Jeff Sheldon | 29.47 | 2012 | ||||
| 5.7 | High Bridge - end of River - Jeep | Dave Harvey | 37.33 | 2017 | Alison Masopust | 41.56 | 2017 | |
| 6.2 | Up Painter Hill rd | Jeff Sheldon | 37.15 | 2015 | Liz Campbell | 39.06 | 2014 | |
| 6.4 | Minors Bridge to Falls road | Hunter McIntyre | 37.02 | 2018 | Alison Masopust | 42.54 | 2015 | |
| 6.5 | Down Hemlock - Up Jeep Trail | Joey Nihill | 42.02 | 2019 | Alison Masopust | 45.09 | 2019 | |
| 6.6 | Sentry Hill | Ken Merrick | 40.36 | 2013 | ||||
| 6.7 | Up Ranney Up Painter | Jeff Sheldon | 41.56 | 2010 | ||||
| 7.25 | DAS BOOT!!!! | Jeff Sheldon | 46.08 | 2014 | Alison Masopust | 48.23 | 2019 | |
| 7.25 | Down Hemlock Up Painter | Jeff Sheldon | 45.59 | 2016 | ||||
| 7.3 | Jeep Trail to Hemlock | Jeff Sheldon | 45.43 | 2010 | ||||
| 8.2 | Judd's Bridge road | Jeff Sheldon | 49.03 | 2014 | ||||
| 8.7 | Battleswamp Preserve | Jeff Sheldon | 59.55 | 2019 | Alison Masopust | 1.01.50 | 2019 | |
| 9.8 | Moosehorn | Bill Goodman | 1.05.31 | 2016 | Alison Masopust | 1.11.38 | 2019 | |
| 11.2 | Up Botsford Hill | Leigh Sorrells | 1.10.00 | 2013 | ||||
| 13.1 | Roxbury Half Marathon | Pat Dennen | 1.22.06 | 2017 | Maddie Leopold | 1:31:11 | 2018 | |
| 26.2 | Roxbury Marathon | Chuck Engle | 2.43.59 | 2015 | Sara Belles | 3:11:57 | 2015 |