| Ragged Mountain | Litchfield, CT | 0 miles | SW |
| Center Hill | Hartford, CT | 3.1 miles | NW |
| Holcomb Hill | Litchfield, CT | 3.4 miles | SE |
| Pine Mountain | Litchfield, CT | 3.4 miles | NE |
| Washington Hill | Litchfield, CT | 3.4 miles | NE |
| Wallens Hill | Litchfield, CT | 3.9 miles | SW |
| Ratlum Mountain | Hartford, CT | 4.3 miles | SE |
| Jones Mountain | Litchfield, CT | 4.7 miles | SE |
| Eno Hill | Litchfield, CT | 4.7 miles | NW |
| Breezy Hill | Hartford, CT | 4.9 miles | SE |
| West Hill | Litchfield, CT | 5.1 miles | SW |
| Spencer Hill | Litchfield, CT | 5.1 miles | SW |
| Pine Cone | Hartford, CT | 5.5 miles | NE |
| Booth Hill | Hartford, CT | 5.6 miles | NE |
| Beecher Hill | Litchfield, CT | 6 miles | NW |
| Morrison Hill | Hartford, CT | 6 miles | NE |
| West Ledge | Hartford, CT | 6.1 miles | SE |
| Panorama Hill | Litchfield, CT | 6.3 miles | NW |
| Weed Hill | Hartford, CT | 6.4 miles | SE |
| Broad Hill | Hartford, CT | 6.6 miles | NE |
| Babb Hill | Litchfield, CT | 7 miles | NW |
| Burr Mountain | Litchfield, CT | 7.1 miles | SW |
| Johnson Hill | Hampden, MA | 7.1 miles | NW |
| Yellow Mountain | Litchfield, CT | 7.1 miles | SW |
| The Hedgehog | Hartford, CT | 7.1 miles | SE |
| Beech Hill | Litchfield, CT | 7.4 miles | NW |
| East Hill | Hartford, CT | 7.4 miles | SE |
| The Sugarloaf | Hartford, CT | 7.4 miles | SE |
| Mount Pisgah | Litchfield, CT | 7.4 miles | NW |
| Sunset Hill | Hampden, MA | 7.5 miles | NW |
| Onion Mountain | Hartford, CT | 7.5 miles | SE |
| Rattlesnake Hill | Hartford, CT | 7.5 miles | SE |
| Platt Hill | Litchfield, CT | 7.7 miles | SW |
| Bushy Hill | Hartford, CT | 7.9 miles | NE |
| Bee Mountain | Litchfield, CT | 8.1 miles | SW |
| Mount Prospect | Berkshire, MA | 8.1 miles | NW |
| Mount Prospect | Litchfield, CT | 8.1 miles | NW |
| Hunting Hill | Hampden, MA | 8.2 miles | NW |
| Babbitt Mountain | Hampden, MA | 8.4 miles | NW |
| Mount Horr | Hartford, CT | 8.5 miles | SE |
| Crag Mountain | Hartford, CT | 8.8 miles | NE |
| Stony Hill | Hartford, CT | 8.8 miles | NE |
| Bull Mountain | Berkshire, MA | 9 miles | NW |
| Garrett Mountain | Litchfield, CT | 9.1 miles | SE |
| Winchell Mountain | Hampden, MA | 9.1 miles | NE |
| South Mountain | Hampden, MA | 9.1 miles | NE |
| Flagg Hill | Litchfield, CT | 9.2 miles | NW |
| Walnut Mountain | Litchfield, CT | 9.2 miles | SW |
| Burgess Mountain | Hampden, MA | 9.3 miles | NW |
| Sweetheart Mountain | Hartford, CT | 9.3 miles | SE |
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