| God's Acre Hill Climb | 0.06 mi | 36 ft | 10.6% |
| Oenoke Main St. to Luke's Wood | 2.95 mi | 203 ft | 1.1% |
| Oenoke Ridge - West Rd to West Rd | 2.73 mi | 148 ft | 0.4% |
| W to Scotts Corners | 2.06 mi | 144 ft | 1.0% |
| West Rd to Country Club | 0.52 mi | 59 ft | 2.1% |
| Country Club to Turtle Back | 0.43 mi | 36 ft | 1.5% |
| Oenoke Sprint | 0.54 mi | 20 ft | 0.7% |
| Oneoke Ridge: Lukes Wood to West | 0.58 mi | -62 ft | -1.4% |
| Louise's Lane Climb | 0.17 mi | 26 ft | 2.6% |
| Westchester Ave: West to Trinity Pass | 0.90 mi | -85 ft | -1.1% |
| Pound Ridge Creek to Triangle | 1.93 mi | 243 ft | 2.2% |
| Rumplestiltskin to 121 | 4.36 mi | 246 ft | 0.1% |
| Rumplestiltskin | 1.30 mi | 256 ft | 3.7% |
| Westchester Ave climb to Parkers | 1.24 mi | 243 ft | 3.7% |
| Fancher-Nursery Climb | 1.08 mi | 184 ft | 3.1% |
| Pound Ridge Cemetary to Nursery | 0.81 mi | 157 ft | 3.2% |
| Descent of The Steps | 2.56 mi | -213 ft | -1.5% |
| Old Stone Hill to 121 | 1.83 mi | -131 ft | -0.8% |
| Sprint to the Old Post Stone Hill Stop | 0.57 mi | -43 ft | -1.1% |
| 121 to Martha Stewart's house | 2.44 mi | 72 ft | 0.6% |
| Pea Pond to Katonah Art Museum | 3.79 mi | -236 ft | -0.8% |
| Martha Stuart Turkey Dinner Sprint | 0.51 mi | 39 ft | 0.3% |
| The New Martha Stewart Turkey Dinner Sprint | 0.40 mi | 39 ft | 0.1% |
| First Goldens Bridge Rd. climb from 35 | 0.56 mi | 98 ft | 3.3% |
| Rt 22 - 35 to the Swan | 4.56 mi | 112 ft | 0.0% |
| Titicus Rd Hill | 0.46 mi | 128 ft | 5.2% |
| Titicus Reservoir | 3.15 mi | 151 ft | 0.9% |
| Titicus - 22 to Delancey | 2.76 mi | 128 ft | 0.9% |
| Norton Road Climb | 1.44 mi | 400 ft | 5.2% |
| 121/116 Climb to Keeler Ln | 0.65 mi | 121 ft | 3.5% |
| 116 to Ridgefield | 5.33 mi | 200 ft | 0.5% |
| Route 116 Wallace Rd to Mananasco Rd. | 1.76 mi | 128 ft | 0.9% |
| Hilltop to Prospect on 116 | 5.36 mi | 207 ft | 0.7% |
| Actual Titicus Road Climb | 0.73 mi | 128 ft | 3.2% |
| Catoonah to the fountain | 0.60 mi | 49 ft | 1.5% |
| Ridgefield to New Canaan | 9.45 mi | -545 ft | -1.1% |
| Rt. 35 to Elmwood via West Lane | 1.23 mi | 82 ft | 0.1% |
| Rt. 35 to Rt. 123 via West Lane and Elmwood | 3.52 mi | -194 ft | -0.3% |
| Elmwood from West to Lockwood | 1.76 mi | -157 ft | -1.4% |
| Recovery Road | 2.25 mi | -154 ft | -0.7% |
| Elmwood Sprint | 0.19 mi | 39 ft | 3.6% |
| Gasoline alley | 0.17 mi | 33 ft | 3.6% |
| 123 to NCCC | 3.09 mi | -118 ft | -0.6% |
| NY New Canaan border south to first stop light | 3.65 mi | -308 ft | -1.6% |
| NC Drag Strip (RT123: Border to Michigan) | 1.09 mi | -49 ft | -0.8% |
| NY-123 Border to Forest | 3.26 mi | -266 ft | -1.5% |
| Country Club to stop light | 1.60 mi | -256 ft | -3.0% |
