| Huggins Gorge | Hartford, CT | 6.7 miles | NE |
| Horseshoe Cove | Hartford, CT | 7.1 miles | SE |
| Hathaway Hollow | Hartford, CT | 13.1 miles | NE |
| Seymour Hollow | Hartford, CT | 13.1 miles | NE |
| Twining Hollow | Hampden, MA | 13.6 miles | NE |
| Mundy Hollow | Hartford, CT | 13.8 miles | NE |
| Sullivan Hollow | Hampden, MA | 15 miles | NE |
| The Gorge | Hampden, MA | 16.6 miles | NE |
| Johnson Hollow | Litchfield, CT | 18.9 miles | SW |
| Peebles Hollow | Hampden, MA | 19.5 miles | NW |
| Cream Hollow | Litchfield, CT | 19.6 miles | NW |
| May Hollow | Hampden, MA | 19.6 miles | NE |
| Dean Ravine | Litchfield, CT | 22 miles | NW |
| Housatonic Valley | Litchfield, CT | 22.9 miles | SW |
| Wildcat Hollow | Litchfield, CT | 23.9 miles | NW |
| Pinnacle Valley | Litchfield, CT | 24.8 miles | SW |
| Quinnipiac Gorge | New Haven, CT | 25.3 miles | SE |
| Marks Hollow | Litchfield, CT | 25.9 miles | SW |
| Guilder Hollow | Berkshire, MA | 25.9 miles | NW |
| Smith Hollow | Berkshire, MA | 26 miles | NW |
| Copper Valley | New Haven, CT | 27.3 miles | SE |
| Tyringham Valley | Berkshire, MA | 27.7 miles | NW |
| Kent Hollow | Litchfield, CT | 28 miles | SW |
| Sages Ravine | Berkshire, CT | 28.3 miles | NW |
| Sages Ravine | Berkshire, MA | 28.3 miles | NW |
| Sages Ravine | Litchfield, CT | 28.4 miles | NW |
| Sages Ravine | Litchfield, MA | 28.4 miles | NW |
| Guilder Hollow | Berkshire, MA | 31 miles | NW |
| Tray Hollow | Tolland, CT | 31.2 miles | NE |
| Indian Hollow | Hampshire, MA | 32.1 miles | NE |
| Ice Glen | Berkshire, MA | 33.3 miles | NW |
| Preechey Hollow | Columbia, NY | 33.6 miles | NW |
| Turkey Hollow | Dutchess, NY | 33.9 miles | SW |
| Housatonic Valley | Litchfield, CT | 34 miles | SW |
| Clatter Valley | Litchfield, CT | 34 miles | SW |
| Mutton Hollow | Dutchess, NY | 36 miles | SW |
| Wildcat Gorge | New Haven, CT | 37 miles | SW |
| Devils Den | Hampshire, MA | 38.4 miles | NE |
| Mansfield Hollow | Tolland, CT | 39.2 miles | SE |
| Boston Hollow | Windham, CT | 39.3 miles | NE |
| Knapp Hollow | Columbia, NY | 39.5 miles | NW |
| Pleasant Valley | Berkshire, MA | 39.7 miles | NW |
| Holland Glen | Hampshire, MA | 39.9 miles | NE |
| Shepard Hollow | Columbia, NY | 40.7 miles | NW |
| Hemlock Valley | Middlesex, CT | 40.8 miles | SE |
| Clove Valley | Dutchess, NY | 41.1 miles | SW |
| Buttermilk Hollow | Fairfield, CT | 42.1 miles | SW |
| Sleepy Hollow | Berkshire, MA | 42.3 miles | NW |
| Guinea Gulf | Franklin, MA | 42.6 miles | NE |
| Dark Hollow | Dutchess, NY | 42.6 miles | SW |
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