| Colebrook Historical Society Building | Litchfield, CT | 0 miles | SE |
| Colebrook Town Garage | Litchfield, CT | 0 miles | NW |
| Colebrook Town Hall | Litchfield, CT | 0 miles | SE |
| Center Fire Station | Litchfield, CT | 1.4 miles | SW |
| Forge Fire Station | Litchfield, CT | 3.1 miles | SE |
| John T Kenney Hitchcock Museum | Litchfield, CT | 4.9 miles | SE |
| Norfolk Historical Society Building | Litchfield, CT | 5.1 miles | SW |
| Norfolk Historical Society Museum | Litchfield, CT | 5.1 miles | SW |
| Norfolk Library | Litchfield, CT | 5.1 miles | SW |
| Norfolk Town Hall | Litchfield, CT | 5.1 miles | SW |
| Beardsley Memorial Library | Litchfield, CT | 5.3 miles | SE |
| Northwestern Connecticut Community College Library | Litchfield, CT | 5.8 miles | SE |
| West New Boston Town Hall | Berkshire, MA | 5.8 miles | NE |
| Hartland Public Library | Hartford, CT | 6.1 miles | NE |
| Tolland Center Town Hall | Hampden, MA | 7.2 miles | NE |
| Old School House Museum | Litchfield, CT | 8.4 miles | SE |
| Hartland Town Hall | Hartford, CT | 9.9 miles | SE |
| New Hartford Free Public Library | Litchfield, CT | 10.3 miles | SE |
| New Hartford Historical Society Museum | Litchfield, CT | 10.3 miles | SE |
| New Hartford Town Hall | Litchfield, CT | 10.3 miles | SE |
| Litchfield County Center for Higher Education | Litchfield, CT | 11.4 miles | SW |
| Torrington Library University of Connecticut | Litchfield, CT | 11.4 miles | SW |
| Mill River Town Hall | Berkshire, MA | 11.8 miles | NW |
| Connecticut Railroad Historical Museum | Litchfield, CT | 12 miles | NW |
| Douglas Library | Litchfield, CT | 12.1 miles | NW |
| C H Pease Museum | Litchfield, CT | 12.1 miles | NW |
| Granville Center Town Hall | Hampden, MA | 12.1 miles | NE |
| Bakerville Library | Litchfield, CT | 12.2 miles | SE |
| North Canaan Town Hall | Litchfield, CT | 12.3 miles | NW |
| Goshen Library | Litchfield, CT | 13.2 miles | SW |
| Goshen Town Offices | Litchfield, CT | 13.2 miles | SW |
| Goshen Historical Society Building | Litchfield, CT | 13.3 miles | SW |
| Goshen Historical Society Library | Litchfield, CT | 13.3 miles | SW |
| Old Goshen Town Hall | Litchfield, CT | 13.3 miles | SW |
| Otis Town Hall | Berkshire, MA | 13.4 miles | NE |
| John Thompson Memorial Library | Litchfield, CT | 13.5 miles | SW |
| Hotchkiss-Fyler House | Litchfield, CT | 13.5 miles | SW |
| David M Hunt Library and School Association | Litchfield, CT | 13.8 miles | SW |
| Monterey Town Hall | Berkshire, MA | 13.8 miles | NW |
| Colonel Ashley House | Berkshire, MA | 13.8 miles | NW |
| Torrington Library | Litchfield, CT | 13.9 miles | SW |
| Canaan Historical Library | Litchfield, CT | 14 miles | SW |
| Canaan Historical Society Library | Litchfield, CT | 14 miles | SW |
| City of Torrington Street Division Garage | Litchfield, CT | 14.3 miles | SW |
| Red Mountain Shelter (historical) | Litchfield, CT | 14.4 miles | SW |
| Sheffield Town Hall | Berkshire, MA | 15.2 miles | NW |
| Roaring Brook Nature Center | Hartford, CT | 15.3 miles | SE |
| Blandford Town Hall | Hampden, MA | 15.3 miles | NE |
| Collinsville Town Hall | Hartford, CT | 15.8 miles | SE |
| Pine Lodge | Litchfield, CT | 15.8 miles | SW |
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