| County Road Trail | Hampden, MA | 15.3 miles | NE |
| Fisher Trail | Hampden, MA | 16.2 miles | NE |
| Richard Trail | Hampden, MA | 16.5 miles | NE |
| Link Trail | Hampden, MA | 16.7 miles | NE |
| Border Trail | Hampden, MA | 17.3 miles | NE |
| Tunxis Trail | Hartford, CT | 17.8 miles | SE |
| Elbow Trail | Berkshire, MA | 18.5 miles | NW |
| Wild Cat Trail | Berkshire, MA | 18.7 miles | NW |
| Indian Trail | Berkshire, MA | 19.5 miles | NW |
| Northrop Trail | Berkshire, MA | 21.6 miles | NW |
| Metacomet Trail | Hartford, CT | 21.8 miles | SE |
| Spruce Hill Trail | Berkshire, MA | 22.3 miles | SE |
| Mattatuck Trail | Litchfield, CT | 23.3 miles | SW |
| Spring Trail | Hampden, MA | 25.1 miles | NE |
| Appalachian National Scenic Trail | Litchfield, CT | 25.2 miles | SW |
| Tunxis Trail | Hartford, CT | 27 miles | SE |
| Mattatuck Trail | New Haven, CT | 27.3 miles | SE |
| East Hartford Cross Country Ski and Jogging Trails | Hartford, CT | 29.7 miles | SE |
| Candlewood Trail | Litchfield, CT | 33.5 miles | SW |
| Taconic Skyline Trail | Berkshire, MA | 35 miles | NW |
| Brickhouse Mountain Trail | Berkshire, MA | 35.6 miles | NW |
| Mattabesset Trail | Middlesex, CT | 35.8 miles | SE |
| Turner Trail | Berkshire, MA | 35.9 miles | NW |
| Naugatuck Trail | New Haven, CT | 37.6 miles | SE |
| Quinnipiac Trail | New Haven, CT | 41.6 miles | SE |
| Washington Trail | Middlesex, CT | 42.2 miles | SE |
| Cheshire Harbor Trail | Berkshire, MA | 43 miles | NW |
| Circle Trail | Berkshire, MA | 43.8 miles | NW |
| Deer Hill Trail | Berkshire, MA | 43.8 miles | NW |
| Regicides Trail | New Haven, CT | 43.9 miles | SE |
| Thunderbolt Ski Trail | Berkshire, MA | 44.2 miles | NW |
| Overlook Trail | Berkshire, MA | 44.4 miles | NW |
| Hopper Trail | Berkshire, MA | 44.4 miles | NW |
| Mattabesset Trail | New Haven, CT | 44.7 miles | SE |
| Stony Ledge Ski Trail | Berkshire, MA | 44.9 miles | NW |
| Busby Trail | Berkshire, MA | 46.1 miles | NE |
| Southeast Hollow Trail | Rensselaer, NY | 47.3 miles | NW |
| Nipmuck Trail | Tolland, CT | 48.2 miles | SE |
| Williams Trail | Berkshire, MA | 48.7 miles | NW |
| Dunbar Brook Trail | Franklin, MA | 49.7 miles | NE |
| Taconic Crest Trail | Bennington, VT | 52.6 miles | NW |
| West Woods Trail | New Haven, CT | 52.9 miles | SE |
| Old Stage Trail | Bennington, VT | 58.6 miles | NE |
| Appalachian National Scenic Trail | Putnam, NY | 59.5 miles | SW |
| Willow Trail | Ulster, NY | 59.8 miles | NW |
| Kelly Camp Trail | Bennington, VT | 59.8 miles | NE |
| Spruceton Trail | Greene, NY | 60.6 miles | NW |
| Ghost Trail | Windham, VT | 60.7 miles | NE |
| Mount Olga Trail | Windham, VT | 60.7 miles | NE |
| Phoenicia Trail | Ulster, NY | 60.9 miles | NW |
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