| Climbing the High School | 0.92 mi | 194 ft | 4.0% |
| road bike rental party | 10.76 mi | 561 ft | 0.8% |
| Peekskill Hollow Rd to Rt 301 | 2.43 mi | 338 ft | 2.6% |
| Little Brother | 0.26 mi | 72 ft | 5.1% |
| Peekskill Hollow Climb at the end | 1.09 mi | 259 ft | 4.0% |
| Big Brother | 0.78 mi | 249 ft | 6.1% |
| The 301 Halfmile Hussle | 0.45 mi | -10 ft | -0.4% |
| Nichols St (W to E) | 1.06 mi | 180 ft | 1.6% |
| Nicols Street Climb | 0.41 mi | 177 ft | 7.9% |
| Nichols Hill | 0.31 mi | 174 ft | 10.2% |
| Bullet Hole (Carmel to Patterson) | 1.78 mi | 190 ft | 1.5% |
| Bullet Hole (Ice Pond to 164) | 1.32 mi | -266 ft | -3.8% |
| Cushman - Mooney Hill | 3.40 mi | 410 ft | 0.9% |
| Cushman - Mooney Hill climb | 2.34 mi | 410 ft | 3.3% |
| Fireside Ct Climb | 0.82 mi | 266 ft | 6.1% |
| Milltown Rd climb from 52 | 0.89 mi | 174 ft | 3.6% |
| 301 to top of Peekskill Hollow | 0.46 mi | 135 ft | 5.5% |
| Peekskill Hollow Rd - Rt 301 to Bryant Pond | 5.78 mi | -417 ft | -1.0% |
| Peekskill Hollow 301 to Gordon | 1.34 mi | -243 ft | -1.7% |
| PH to 301 | 1.98 mi | -259 ft | -1.4% |
| Peekskill Hollow southwest to Mill St | 8.77 mi | -489 ft | -0.8% |
| Peekskill Hollow Towards Peekskill | 11.28 mi | -623 ft | -0.8% |
| Peekskill hollow downhill to Adams corners. All out. | 8.12 mi | -463 ft | -1.1% |
| White Trash Ramble! | 1.75 mi | -62 ft | -0.7% |
| Love to Cindy and Wilma | 0.75 mi | 105 ft | 2.3% |
| Old Oregon Rd to Locus Ave | 1.83 mi | -62 ft | -0.3% |
| Locus to Frost Lane Via Division St | 1.15 mi | 56 ft | 0.8% |
| Matty's Climb Home | 0.32 mi | 161 ft | 9.4% |
