| Calvin Coolidge State Park | Windsor, VT | 3.9 miles | SW |
| South Woodstock Historic District | Windsor, VT | 4.3 miles | SE |
| Coolidge State Park | Windsor, VT | 4.3 miles | SW |
| Plymouth Notch Historic District | Windsor, VT | 5.6 miles | SW |
| Calvin Coolidge Homestead District | Windsor, VT | 5.8 miles | SW |
| Faulknet Park | Windsor, VT | 5.8 miles | NE |
| Billings Park and Trails | Windsor, VT | 6 miles | NE |
| The Green | Windsor, VT | 6 miles | NE |
| Vail Field | Windsor, VT | 6 miles | NE |
| Woodstock Village Historic District | Windsor, VT | 6 miles | NE |
| Marsh-Billings-Rockefeller National Historical Park | Windsor, VT | 6 miles | NE |
| Tribou Park | Windsor, VT | 6.4 miles | NE |
| Billings Farm Museum | Windsor, VT | 6.6 miles | NE |
| Camp Plymouth State Park | Windsor, VT | 7.7 miles | SW |
| Knapp Brook Wildlife Management Area | Windsor, VT | 8.9 miles | SE |
| Plymsbury Wildlife Management Area | Rutland, VT | 9.2 miles | SW |
| Valley Park | Rutland, VT | 10.1 miles | NW |
| Silver Lake State Park | Windsor, VT | 11 miles | NE |
| Lew Newall Wildlife Management Area | Rutland, VT | 11.2 miles | NW |
| Little Ascutney State Wildlife Manage Area | Windsor, VT | 11.3 miles | SE |
| Amity Pond Natural Area | Windsor, VT | 11.6 miles | NE |
| Gifford Woods Natural Area | Rutland, VT | 11.8 miles | NW |
| Giffords Woods State Forest Park | Rutland, VT | 12 miles | NW |
| Ascutney State Park | Windsor, VT | 12.7 miles | SE |
| Saint Gaudens National Historic Site | Sullivan, NH | 13.1 miles | SE |
| Dorsey Park | Windsor, VT | 13.1 miles | SW |
| North Hartland Dam Recreation Area | Windsor, VT | 13.1 miles | NE |
| Saint-Gaudens National Historic Site | Sullivan, NH | 13.2 miles | SE |
| Windsor Village Historic District | Windsor, VT | 13.3 miles | SE |
| Hawks Mountain Wildlife Management Area | Windsor, VT | 13.5 miles | SE |
| Chase Island State Wildlife Management Area | Sullivan, NH | 13.6 miles | SE |
| Cornish State Wildlife Management Area | Sullivan, NH | 13.7 miles | SE |
| Weathersfield Center Historic District | Windsor, VT | 15.4 miles | SE |
| Memorial Park | Windsor, VT | 15.4 miles | NE |
| White River Junction Historic District | Windsor, VT | 15.8 miles | NE |
| White River Wildlife Management Area | Windsor, VT | 16 miles | NE |
| North Springfield Lake Recreation Area | Windsor, VT | 16 miles | SE |
| Stockbridge Common Historic District | Windsor, VT | 16.2 miles | NW |
| Wilgus State Park | Windsor, VT | 16.4 miles | SE |
| Rood State Park | Windsor, VT | 16.6 miles | NW |
| Frost Park | Windsor, VT | 16.8 miles | NE |
| Springfield Nature Area | Windsor, VT | 17 miles | SE |
| Northwood Park | Rutland, VT | 17.3 miles | NW |
| Whites Playground | Rutland, VT | 17.7 miles | NW |
| Main Street Park | Rutland, VT | 17.9 miles | NW |
| Bethel Village Historic District | Windsor, VT | 18 miles | NW |
| Rutland Courthouse Historic District | Rutland, VT | 18.1 miles | NW |
| Rutland Downtown Historic District | Rutland, VT | 18.2 miles | NW |
| Norwich Green | Windsor, VT | 18.3 miles | NE |
| Norwich Village Historic District | Windsor, VT | 18.4 miles | NE |
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