| 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% |
