| Twining Hollow | Hampden, MA | 11 miles | NE |
| Cream Hollow | Litchfield, CT | 12.7 miles | SW |
| Huggins Gorge | Hartford, CT | 13.3 miles | SE |
| Johnson Hollow | Litchfield, CT | 13.6 miles | SW |
| Sullivan Hollow | Hampden, MA | 13.9 miles | NE |
| Peebles Hollow | Hampden, MA | 13.9 miles | NE |
| Guilder Hollow | Berkshire, MA | 14 miles | NW |
| Wildcat Hollow | Litchfield, CT | 14 miles | SW |
| Smith Hollow | Berkshire, MA | 14.1 miles | NW |
| Dean Ravine | Litchfield, CT | 14.2 miles | SW |
| The Gorge | Hampden, MA | 14.7 miles | NE |
| Tyringham Valley | Berkshire, MA | 16.6 miles | NW |
| Housatonic Valley | Litchfield, CT | 16.9 miles | SW |
| Sages Ravine | Berkshire, CT | 17.3 miles | NW |
| Sages Ravine | Berkshire, MA | 17.3 miles | NW |
| Sages Ravine | Litchfield, CT | 17.5 miles | NW |
| Sages Ravine | Litchfield, MA | 17.5 miles | NW |
| Horseshoe Cove | Hartford, CT | 18.9 miles | SE |
| Guilder Hollow | Berkshire, MA | 19.4 miles | NW |
| Ice Glen | Berkshire, MA | 21.7 miles | NW |
| Seymour Hollow | Hartford, CT | 22.4 miles | SE |
| May Hollow | Hampden, MA | 22.5 miles | NE |
| Preechey Hollow | Columbia, NY | 22.7 miles | NW |
| Hathaway Hollow | Hartford, CT | 22.8 miles | SE |
| Mundy Hollow | Hartford, CT | 23.7 miles | SE |
| Pinnacle Valley | Litchfield, CT | 24.2 miles | SW |
| Marks Hollow | Litchfield, CT | 25.3 miles | SW |
| Kent Hollow | Litchfield, CT | 27.1 miles | SW |
| Indian Hollow | Hampshire, MA | 27.1 miles | NE |
| Knapp Hollow | Columbia, NY | 27.8 miles | NW |
| Turkey Hollow | Dutchess, NY | 27.9 miles | SW |
| Pleasant Valley | Berkshire, MA | 28.7 miles | NW |
| Shepard Hollow | Columbia, NY | 28.8 miles | NW |
| Sleepy Hollow | Berkshire, MA | 30.9 miles | NW |
| Mutton Hollow | Dutchess, NY | 31.1 miles | SW |
| Devils Den | Hampshire, MA | 33.9 miles | NE |
| Housatonic Valley | Litchfield, CT | 35.1 miles | SW |
| Clatter Valley | Litchfield, CT | 35.3 miles | SW |
| Quinnipiac Gorge | New Haven, CT | 35.6 miles | SE |
| Clove Valley | Dutchess, NY | 37.1 miles | SW |
| Copper Valley | New Haven, CT | 37.2 miles | SE |
| Goodrich Hollow | Berkshire, MA | 37.6 miles | NW |
| Dark Hollow | Dutchess, NY | 38.1 miles | SW |
| Goodrich Hollow | Rensselaer, MA | 38.2 miles | NW |
| Goodrich Hollow | Rensselaer, NY | 38.2 miles | NW |
| Guinea Gulf | Franklin, MA | 38.2 miles | NE |
| Tray Hollow | Tolland, CT | 38.3 miles | NE |
| Pond Gut | Dutchess, NY | 38.8 miles | SW |
| Doty Hollow | Rensselaer, MA | 39.2 miles | NW |
| Doty Hollow | Rensselaer, NY | 39.2 miles | NW |
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