| Dunbar Brook Trail | Franklin, MA | 14.8 miles | NW |
| Busby Trail | Berkshire, MA | 16.9 miles | NW |
| Mount Olga Trail | Windham, VT | 17.7 miles | NW |
| Sunset Trail | Windham, VT | 17.7 miles | NE |
| Ghost Trail | Windham, VT | 17.9 miles | NW |
| Sunrise Trail | Windham, VT | 18 miles | NE |
| Spring Trail | Hampden, MA | 20.7 miles | SW |
| Thunderbolt Ski Trail | Berkshire, MA | 21.1 miles | NW |
| Cheshire Harbor Trail | Berkshire, MA | 21.7 miles | NW |
| Overlook Trail | Berkshire, MA | 22.2 miles | NW |
| Circle Trail | Berkshire, MA | 22.9 miles | NW |
| Deerfield Ridge Trail | Windham, VT | 22.9 miles | NW |
| Deer Hill Trail | Berkshire, MA | 23 miles | NW |
| Kelly Camp Trail | Bennington, VT | 23 miles | NW |
| Hopper Trail | Berkshire, MA | 23.1 miles | NW |
| Stony Ledge Ski Trail | Berkshire, MA | 23.9 miles | NW |
| Old Stage Trail | Bennington, VT | 24.2 miles | NW |
| Deerfield Ridge Trail | Windham, VT | 24.2 miles | NW |
| Molly Stark Trail | Bennington, VT | 26 miles | NW |
| Atwood Trail | Bennington, VT | 26.4 miles | NW |
| Williams Trail | Berkshire, MA | 27.5 miles | NW |
| Southeast Hollow Trail | Rensselaer, NY | 29 miles | NW |
| Taconic Crest Trail | Bennington, VT | 29.1 miles | NW |
| Turner Trail | Berkshire, MA | 29.6 miles | SW |
| Bald Mountain Trail | Bennington, VT | 30.3 miles | NW |
| Brickhouse Mountain Trail | Berkshire, MA | 30.7 miles | SW |
| Border Trail | Hampden, MA | 30.9 miles | SW |
| Richard Trail | Hampden, MA | 31.6 miles | SW |
| Link Trail | Hampden, MA | 31.7 miles | SW |
| Deerfield Trail | Windham, VT | 31.8 miles | NW |
| West Ridge Trail | Bennington, VT | 31.9 miles | NW |
| Fisher Trail | Hampden, MA | 32 miles | SW |
| Taconic Skyline Trail | Berkshire, MA | 32 miles | SW |
| County Road Trail | Hampden, MA | 33.2 miles | SW |
| Cooridor 7 | Windham, VT | 34.3 miles | NW |
| Overlook Trail | Windham, VT | 35.1 miles | NW |
| Branch Pond Trail | Bennington, VT | 35.3 miles | NW |
| Railroad Bed Trail | Windham, VT | 35.8 miles | NW |
| Marlboro Trail | Cheshire, NH | 36 miles | NE |
| White Arrow Trail | Cheshire, NH | 36.5 miles | NE |
| Healing Springs Nature Trail | Bennington, VT | 36.8 miles | NW |
| Farmers Trail | Cheshire, NH | 36.9 miles | NE |
| Red Cross Trail | Cheshire, NH | 37 miles | NE |
| White Dot Trail | Cheshire, NH | 37.2 miles | NE |
| Hamilton Falls Trail | Windham, VT | 37.3 miles | NW |
| Cascade Link Trail | Cheshire, NH | 37.7 miles | NE |
| Harling Trail | Cheshire, NH | 37.8 miles | NE |
| Wild Cat Trail | Berkshire, MA | 38 miles | SW |
| Lye Brook Trail | Bennington, VT | 38 miles | NW |
| Pumpelly Trail | Cheshire, NH | 38.4 miles | NE |
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