| Middle Covered Bridge | Windsor, VT | 8.3 miles | SE |
| Elm Street Bridge | Windsor, VT | 8.4 miles | SE |
| Middle Covered Bridge | Windsor, VT | 8.5 miles | SE |
| Mill Bridge | Windsor, VT | 8.7 miles | SE |
| Iron Bridge | Windsor, VT | 8.9 miles | SE |
| Lincoln Covered Bridge | Windsor, VT | 9 miles | SE |
| Taftsville Covered Bridge | Windsor, VT | 10 miles | SE |
| Gilead Brook Covered Bridge | Windsor, VT | 10.3 miles | NW |
| Kingsbury Covered Bridge | Orange, VT | 10.9 miles | NE |
| Howe Covered Bridge | Orange, VT | 11.4 miles | NE |
| Quechee Covered Bridge | Windsor, VT | 11.4 miles | SE |
| Quechee Gorge Bridge | Windsor, VT | 12.2 miles | SE |
| Cilley Covered Bridge | Orange, VT | 12.2 miles | NE |
| Mill Covered Bridge | Orange, VT | 13.1 miles | NE |
| Braley Covered Bridge | Orange, VT | 13.5 miles | NE |
| C K Smith Covered Bridge | Orange, VT | 14.4 miles | NE |
| Larkin Covered Bridge | Orange, VT | 15.6 miles | NE |
| Ottauquechee River Bridge | Windsor, VT | 15.8 miles | SE |
| Ledyard Free Bridge | Grafton, NH | 16.1 miles | SE |
| Willard Covered Bridge | Windsor, VT | 16.3 miles | SE |
| Martins Mill Covered Bridge | Windsor, VT | 17.4 miles | SE |
| Flint Covered Bridge | Orange, VT | 17.4 miles | NE |
| Moxley Covered Bridge | Orange, VT | 17.7 miles | NE |
| Twin Bridge (historical) | Rutland, VT | 18.5 miles | SW |
| Union Village Covered Bridge | Orange, VT | 18.7 miles | NE |
| Brown Covered Bridge | Rutland, VT | 18.7 miles | SW |
| Blow-Me-Down Bridge | Sullivan, NH | 18.9 miles | SE |
| Bests Covered Bridge | Windsor, VT | 19.4 miles | SE |
| Bowers Covered Bridge | Windsor, VT | 19.4 miles | SE |
| Thetford Center Covered Bridge | Orange, VT | 19.7 miles | NE |
| Colburn Bridge | Rutland, VT | 20.1 miles | SW |
| Cooley Covered Bridge | Rutland, VT | 20.4 miles | SW |
| Packard Hill Bridge | Grafton, NH | 20.7 miles | SE |
| Cornish Bridge | Sullivan, NH | 21 miles | SE |
| Cornish-Windsor Bridge | Sullivan, NH | 21.1 miles | SE |
| Cornish Bridge | Windsor, VT | 21.1 miles | SE |
| Gorham Bridge | Rutland, VT | 21.2 miles | SW |
| Meriden Bridge | Sullivan, NH | 21.3 miles | SE |
| Kingsley Covered Bridge | Rutland, VT | 21.4 miles | SW |
| Hammond Covered Bridge | Rutland, VT | 21.6 miles | SW |
| Depot Covered Bridge | Rutland, VT | 21.7 miles | SW |
| Brookfield Floating Bridge | Orange, VT | 21.9 miles | NE |
| Dingleton Hill Bridge | Sullivan, NH | 22 miles | SE |
| Blacksmith Shop Bridge | Sullivan, NH | 22.5 miles | SE |
| Upper Falls Covered Bridge | Windsor, VT | 23.2 miles | SE |
| Dean Bridge | Rutland, VT | 24.2 miles | NW |
| Edgell Bridge | Grafton, NH | 24.7 miles | NE |
| Sanderson Bridge | Rutland, VT | 25 miles | NW |
| Lottery Bridge | Sullivan, NH | 25.3 miles | SE |
| Downers Covered Bridge | Windsor, VT | 26.4 miles | SE |
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