| Hales Hill | Berkshire, MA | 1.4 miles | SE |
| The Pinnacle | Berkshire, MA | 1.4 miles | SW |
| Cheshire Harbor Hill | Berkshire, MA | 1.9 miles | SW |
| Cole Mountain | Berkshire, MA | 2.7 miles | SW |
| Mount Greylock | Berkshire, MA | 2.7 miles | NW |
| Mount Fitch | Berkshire, MA | 3.1 miles | NW |
| Saddle Ball Mountain | Berkshire, MA | 3.4 miles | NW |
| Mount Amos | Berkshire, MA | 3.4 miles | SW |
| Stafford Hill | Berkshire, MA | 3.6 miles | SE |
| Mount Williams | Berkshire, MA | 3.9 miles | NW |
| Stony Ledge | Berkshire, MA | 4.1 miles | NW |
| Spruce Hill | Berkshire, MA | 4.3 miles | NE |
| Mount Prospect | Berkshire, MA | 4.3 miles | NW |
| Rounds Rock | Berkshire, MA | 4.5 miles | SW |
| Lewis Hill | Berkshire, MA | 4.7 miles | SE |
| Borden Mountain | Berkshire, MA | 4.9 miles | SE |
| The Cobbles | Berkshire, MA | 5.1 miles | SW |
| Spruce Hill | Berkshire, MA | 5.1 miles | NE |
| Sugarloaf | Berkshire, MA | 5.5 miles | SW |
| Woodchuck Hill | Berkshire, MA | 5.5 miles | SE |
| Chadbournes Knoll | Berkshire, MA | 5.5 miles | NW |
| E Parmalee Prentice Mountain | Berkshire, MA | 6 miles | NW |
| The Cobble | Berkshire, MA | 6 miles | NW |
| The Cobble | Berkshire, MA | 6 miles | NW |
| Flat Rock Hill | Berkshire, MA | 6.1 miles | NE |
| Pratt Hill | Berkshire, MA | 6.3 miles | SW |
| Brodie Mountain | Berkshire, MA | 6.4 miles | NW |
| Whitcomb Hill | Berkshire, MA | 6.6 miles | NE |
| North Mountain | Berkshire, MA | 6.6 miles | SW |
| Windsor Hill | Berkshire, MA | 7 miles | SE |
| Stone Hill | Berkshire, MA | 7.1 miles | NW |
| Phelps Knoll | Berkshire, MA | 7.1 miles | NW |
| Weston Mountain | Berkshire, MA | 7.2 miles | SE |
| Savage Hill | Berkshire, MA | 7.4 miles | SW |
| Pine Cobble | Berkshire, MA | 7.4 miles | NW |
| East Mountain | Berkshire, MA | 7.5 miles | NW |
| Rowe Lot Hill | Franklin, MA | 7.5 miles | SE |
| Bald Mountain | Berkshire, MA | 7.6 miles | NW |
| Fobes Hill | Berkshire, MA | 7.6 miles | SE |
| The Noppet | Berkshire, MA | 7.9 miles | SW |
| West Hill | Berkshire, MA | 7.9 miles | SE |
| East Mountain | Berkshire, MA | 7.9 miles | SW |
| Pine Cobble | Berkshire, MA | 8 miles | NE |
| Crum Hill | Franklin, MA | 8.1 miles | NE |
| Clark Mountain | Berkshire, MA | 8.1 miles | NE |
| Blackpoll Mountain | Berkshire, MA | 8.1 miles | NE |
| Farnams Hill | Berkshire, MA | 8.2 miles | SW |
| Buxton Hill | Berkshire, MA | 8.2 miles | NW |
| Beoadic Mountain | Berkshire, MA | 8.2 miles | SW |
| Bee Hill | Berkshire, MA | 8.2 miles | NW |
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