| Walley Bridge | Berkshire, MA | 7.2 miles | NW |
| Moody Bridge | Berkshire, MA | 8.5 miles | NW |
| Florida Bridge | Berkshire, MA | 8.8 miles | NE |
| Florida Bridge | Franklin, MA | 8.8 miles | NE |
| Bissell Covered Bridge | Franklin, MA | 12.8 miles | NE |
| Medburyville Bridge | Windham, VT | 20.1 miles | NE |
| Silk Road Covered Bridge | Bennington, VT | 20.7 miles | NW |
| Arthur Smith Covered Bridge | Franklin, MA | 20.8 miles | NE |
| Paper Mill Village Bridge | Bennington, VT | 21.1 miles | NW |
| Henry Covered Bridge | Bennington, VT | 21.3 miles | NW |
| Burkeville Covered Bridge | Franklin, MA | 22.3 miles | SE |
| Green River Covered Bridge | Windham, VT | 25.5 miles | NE |
| Stillwater Bridge | Franklin, MA | 25.7 miles | SE |
| Pumping Station Covered Bridge | Franklin, MA | 25.9 miles | SE |
| Buskirks Covered Bridge | Washington, NY | 28.3 miles | NW |
| Sunderland Bridge | Franklin, MA | 29.3 miles | SE |
| Chiselville Covered Bridge | Bennington, VT | 31.3 miles | NW |
| Creamery Covered Bridge | Windham, VT | 31.5 miles | NE |
| Williamsville Covered Bridge | Windham, VT | 31.8 miles | NE |
| French King Bridge | Franklin, MA | 32.2 miles | SE |
| Eagleville Covered Bridge | Washington, NY | 33.5 miles | NW |
| West Dummerston Covered Bridge | Windham, VT | 33.8 miles | NE |
| Arlington Green Covered Bridge | Bennington, VT | 33.9 miles | NW |
| Schell Bridge | Franklin, MA | 34.5 miles | NE |
| Mosher Bridge | Albany, NY | 35.8 miles | SW |
| Old Covered Bridge | Berkshire, MA | 36.3 miles | SW |
| Scott Covered Bridge | Windham, VT | 36.6 miles | NE |
| Jericho Bridge | Albany, NY | 37 miles | SW |
| Ashuelot Bridge | Cheshire, NH | 37.1 miles | NE |
| Covered Bridge | Berkshire, MA | 37.1 miles | SW |
| Black Grocery Bridge | Columbia, NY | 38.1 miles | SW |
| West Townshend Stone Arch Bridge | Windham, VT | 38.3 miles | NE |
| Hortons Bridge | Hampden, MA | 38.6 miles | SE |
| Simpsonville Stone Arch Bridge | Windham, VT | 39.1 miles | NE |
| Sacketts Brook Stone Arch Bridge | Windham, VT | 39.1 miles | NE |
| East Putney Brook Stone Arch Bridge | Windham, VT | 41.4 miles | NE |
| Coombs Bridge | Cheshire, NH | 42 miles | NE |
| Bryants Bridge | Saratoga, NY | 42.6 miles | NW |
| State Bridge | Cheshire, NH | 42.7 miles | NE |
| Staffords Bridge | Saratoga, NY | 42.9 miles | NW |
| Robinson Bridge | Hampden, MA | 43.2 miles | SE |
| Freemans Bridge | Schenectady, NY | 43.6 miles | NW |
| North End Bridge | Hampden, MA | 43.9 miles | SE |
| West Swanzey Bridge | Cheshire, NH | 43.9 miles | NE |
| Dutchers Bridge | Litchfield, CT | 44.2 miles | SW |
| Western Gateway Bridge | Schenectady, NY | 44.5 miles | NW |
| Memorial Bridge | Hampden, MA | 44.9 miles | SE |
| Calvin Coolidge Bridge | Hampshire, MA | 45 miles | SE |
| Emerald Lake Natural Bridge | Bennington, VT | 45.6 miles | NE |
| Moore Bridge | Litchfield, CT | 46 miles | SE |
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