| Harrison St. to Clarke's Gap Climb | 4,25 mi | 312 ft | 1,4 % |
| Leesburg to Route 9 Hill | 4,01 mi | 285 ft | 1,3 % |
| Harrison Street to Stop Sign | 1,88 mi | 131 ft | 1,3 % |
| The Hill....ish | 3,11 mi | 243 ft | 1,5 % |
| Catoctin to Clarks Gap | 3,26 mi | 236 ft | 1,4 % |
| W&OD: Catoctin Circle to Dry Mill | 2,88 mi | 194 ft | 1,3 % |
| Leesburg - Purceville | 9,55 mi | 249 ft | 0,4 % |
| Catoctin Circle to Top of Clark's Gap | 3,27 mi | 259 ft | 1,5 % |
| W&OD from LCHS to Dry Mill | 2,67 mi | 194 ft | 1,4 % |
| Hill West of Leesburg | 2,75 mi | 240 ft | 1,5 % |
| Leesburg Mountain | 2,33 mi | 167 ft | 1,4 % |
| WOD along Dry Mill Climb | 2,43 mi | 161 ft | 1,2 % |
| New Clake's Gap Climb from Rt 7 Overpass | 2,47 mi | 194 ft | 1,4 % |
| Leesburg 7 overpass to top of John Deere Hill | 6,24 mi | 203 ft | 0,2 % |
| Rt 7 To Clark's Gap | 2,46 mi | 187 ft | 1,4 % |
| Tom's Rte 7 Overpass to Dry Mill rock | 2,10 mi | 157 ft | 1,4 % |
| Rest Area to Top of Hill | 1,74 mi | 138 ft | 1,5 % |
| Uphill and straight | 0,63 mi | 52 ft | 1,5 % |
| W&OD Paeonian Springs to Hamilton | 1,74 mi | -108 ft | -1,2 % |
| Paeonian Springs to Hamilton | 1,75 mi | -89 ft | -0,9 % |
| W&OD Paeonian springs to Hamilton Station | 1,61 mi | -85 ft | -1,0 % |
| W&OD Hamilton to Purcellville | 3,70 mi | 115 ft | 0,5 % |
| Purcellville WOD Climb | 1,41 mi | 102 ft | 1,2 % |
| John Deere Hill | 1,03 mi | 92 ft | 1,7 % |
| Safe W&OD climb to Purcellville | 1,06 mi | 95 ft | 1,7 % |
| 709 To Belkin Pike | 1,08 mi | 92 ft | 1,6 % |
| W&OD: Ivandale to 287 | 1,09 mi | 98 ft | 1,7 % |
| TECC TDF Challenge Green Jersey points | 0,81 mi | 79 ft | 1,7 % |
| E Loudoun Valley Dr Climb | 0,31 mi | 315 ft | 19,3 % |
| Raflo Run | 10,51 mi | -315 ft | -0,4 % |
| Purcellville to Paeonian Springs, VA | 5,97 mi | 148 ft | 0,0 % |
| Purcellville WOD Downhill | 1,47 mi | -121 ft | -1,6 % |
| Milepost 43 to Paeonian Train Shelter | 3,80 mi | 128 ft | 0,0 % |
| Purcellville - 287 to Ivandale | 0,87 mi | -85 ft | -1,9 % |
| Safest Downhill from P'ville | 1,86 mi | -98 ft | -0,8 % |
| Pick me up | 2,25 mi | 112 ft | 0,9 % |
| Deliver The Mail - All Up Hill - No Crossings | 1,52 mi | 85 ft | 1,1 % |
| W&OD Corkscrew to Leesburg | 3,26 mi | -256 ft | -1,5 % |
| Clarks Gap Downhill - no road crossing | 2,52 mi | -197 ft | -1,5 % |
| A really safe segment that only an idiot would mark as unsafe from Clark's Gap to Catoctin | 2,91 mi | -210 ft | -1,4 % |
| This segment has been flagged as hazardous. | 2,88 mi | -194 ft | -1,3 % |
| W&OD trail (Dry Mill to Rt. 7) | 2,30 mi | -171 ft | -1,3 % |
| Dry Mill to LCH | 2,85 mi | -187 ft | -1,2 % |
| W&OD Dry Mill to LCHS | 2,75 mi | -197 ft | -1,3 % |
| gap fox | 2,20 mi | -157 ft | -1,3 % |
| Downhill and straight | 0,84 mi | -69 ft | -1,5 % |
| 4H to LCHS. No stop signs. | 2,34 mi | -164 ft | -1,3 % |
| Ralph's Int'l Speedway | 0,63 mi | -33 ft | -0,8 % |
| S King Sprint | 1,23 mi | -98 ft | -1,5 % |
| Transition Triathlon Test Ride Return | 0,70 mi | -49 ft | -1,3 % |
