| Fuller Bridge | Litchfield, CT | 10.2 miles | SW |
| Dutchers Bridge | Litchfield, CT | 12.5 miles | NW |
| Bulls Bridge Covered Bridge | Litchfield, CT | 13.8 miles | SW |
| Gaylord Bridge | Litchfield, CT | 14.5 miles | SW |
| Boardmans Bridge | Litchfield, CT | 17.1 miles | SW |
| Mill Pond Bridge | Litchfield, CT | 17.5 miles | NE |
| Reynolds Bridge | Litchfield, CT | 17.8 miles | SE |
| Moore Bridge | Litchfield, CT | 18.7 miles | NE |
| Gilbert Bridge | Litchfield, CT | 18.8 miles | NE |
| Kingdom Bridge | Litchfield, CT | 19.5 miles | NE |
| Covered Bridge | Berkshire, MA | 19.6 miles | NW |
| Lovers Leap Bridge | Litchfield, CT | 19.8 miles | SW |
| Frost Bridge | Litchfield, CT | 20.3 miles | SE |
| Minor Bridge | Litchfield, CT | 20.4 miles | SE |
| Old Covered Bridge | Berkshire, MA | 20.7 miles | NW |
| Perry Bridge | Hartford, CT | 23 miles | SE |
| Pierce Bridge | Hartford, CT | 23.8 miles | SE |
| Black Grocery Bridge | Columbia, NY | 24.7 miles | NW |
| Sherman Bridge | Fairfield, CT | 25 miles | SW |
| Montfor Bridge | Dutchess, NY | 26.4 miles | SW |
| Stringham Bridge | Dutchess, NY | 26.5 miles | SW |
| Pequabuck Bridge | Hartford, CT | 26.5 miles | SE |
| Old Grays Bridge | Fairfield, CT | 26.8 miles | SW |
| Salem Bridge | New Haven, CT | 27.4 miles | SE |
| Stanley Simon Bridge | Fairfield, CT | 28 miles | SW |
| Barn Plain Bridge | Fairfield, CT | 29.8 miles | SW |
| Spoonville Bridge | Hartford, CT | 30.5 miles | NE |
| Pine Bridge | New Haven, CT | 30.7 miles | SE |
| Beech Swamp Bridge | Hartford, CT | 31.5 miles | SE |
| George Brown Bridge | Dutchess, NY | 31.6 miles | SW |
| Sheeps Bridge (historical) | Hartford, CT | 32.4 miles | SE |
| Gurney Bridge | Hartford, CT | 32.7 miles | SE |
| Mid-Hudson Bridge | Ulster, NY | 32.7 miles | SW |
| Broad Street Bridge | New Haven, CT | 32.8 miles | SE |
| Kingston-Rhinecliff Bridge | Ulster, NY | 33.3 miles | NW |
| Hortons Bridge | Hampden, MA | 34.7 miles | NE |
| Founders Bridge | Hartford, CT | 34.7 miles | SE |
| Bulkeley Bridge | Hartford, CT | 34.7 miles | SE |
| Folly Bridge | Hartford, CT | 35.1 miles | SE |
| Kirby Bridge | Hartford, CT | 35.4 miles | SE |
| Charter Oak Bridge | Hartford, CT | 35.4 miles | SE |
| Bissell Bridge | Hartford, CT | 35.5 miles | SE |
| William Putnam Memorial Bridge | Middlesex, CT | 36.6 miles | SE |
| Mill's Bridge | Westchester, NY | 37 miles | SW |
| Dexter Cuffin Junior Bridge | Hartford, CT | 37.2 miles | NE |
| Deans Bridge | Westchester, NY | 37.7 miles | SW |
| Rip Van Winkle Bridge | Columbia, NY | 38.1 miles | NW |
| Mansfield Bridge | New Haven, CT | 38.4 miles | SE |
| Enfield Bridge (historical) | Hartford, CT | 38.8 miles | NE |
| Arrigoni Bridge | Middlesex, CT | 39.6 miles | SE |
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