| Little Sandy Trail | Clackamas, OR | 11.6 miles | NE |
| Sewer Trail | Multnomah, OR | 15.2 miles | NE |
| Griffis Creek Trail | Clackamas, OR | 16.4 miles | NE |
| Reservoir Trail | Multnomah, OR | 17.5 miles | NE |
| Cougar Trail | Multnomah, OR | 17.6 miles | NE |
| Aschoff Buttes Trail | Clackamas, OR | 17.8 miles | NE |
| Damsite Trail | Multnomah, OR | 18.3 miles | NE |
| Old Baldy Trail | Clackamas, OR | 19.4 miles | SE |
| Fanton Plaza Trail | Clackamas, OR | 19.7 miles | SE |
| Big Bend Trail | Multnomah, OR | 20 miles | NE |
| Memaloose Trail | Clackamas, OR | 20.1 miles | SE |
| Plaza Trail | Clackamas, OR | 20.1 miles | SE |
| Arrah Wanna Trail | Clackamas, OR | 20.2 miles | SE |
| Larson Way Trail | Clackamas, OR | 20.6 miles | SE |
| Eagle Creek Cutoff | Clackamas, OR | 20.7 miles | SE |
| Bonanza Trail | Clackamas, OR | 21.2 miles | SE |
| Coffman Camp Trail | Clackamas, OR | 21.8 miles | SE |
| Nesmith Point Trail | Multnomah, OR | 22.1 miles | NE |
| Wanderers Peak Trail | Clackamas, OR | 22.4 miles | SE |
| Salmon Mountain Trail | Clackamas, OR | 23 miles | SE |
| Thimble Mountain Trail | Clackamas, OR | 23.3 miles | NE |
| Dry Ridge Trail | Clackamas, OR | 23.6 miles | SE |
| South Fork Ridge Trail | Clackamas, OR | 23.7 miles | SE |
| Corral Springs Trail | Clackamas, OR | 24.2 miles | SE |
| West Zigzag Mountain Trail | Clackamas, OR | 24.3 miles | SE |
| Clear Creek Way Trail | Clackamas, OR | 24.6 miles | NE |
| Tanner Butte Trail | Multnomah, OR | 24.8 miles | NE |
| Tanner Cutoff Trail | Multnomah, OR | 25 miles | NE |
| Salmon Butte Trail | Clackamas, OR | 25.1 miles | SE |
| Eagle Tanner Trail | Hood River, OR | 25.5 miles | NE |
| Hunchback Mountain Trail | Clackamas, OR | 25.6 miles | SE |
| Flag Mountain Trail | Clackamas, OR | 25.7 miles | SE |
| Table Mountain Trail | Multnomah, OR | 25.9 miles | NE |
| Horseshoe Ridge Trail | Clackamas, OR | 26.3 miles | SE |
| Bull Run Lake Trail | Multnomah, OR | 26.6 miles | NE |
| Hambone Trail | Clackamas, OR | 26.6 miles | SE |
| Cool Creek Trail | Clackamas, OR | 26.7 miles | SE |
| Washougal Trail | Skamania, WA | 26.9 miles | NE |
| Blazed Alder Way Trail | Clackamas, OR | 27 miles | NE |
| Cripple Creek Trail | Clackamas, OR | 27 miles | SE |
| Still Creek Trail | Clackamas, OR | 27 miles | SE |
| Cast Creek Trail | Clackamas, OR | 27.1 miles | SE |
| Chitwood Trail | Clackamas, OR | 27.5 miles | NE |
| Huckleberry Mountain Trail | Hood River, OR | 27.5 miles | NE |
| Roaring River Trail | Clackamas, OR | 27.5 miles | SE |
| Devils Canyon Trail | Clackamas, OR | 27.8 miles | SE |
| Cold Spring Trail | Clackamas, OR | 28 miles | SE |
| Portage Trail | Clackamas, OR | 28.2 miles | SE |
| Lost Lake Butte Trail | Hood River, OR | 28.5 miles | NE |
| Green Leaf Trail | Skamania, WA | 28.5 miles | NE |
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