There are numerous crossings of the Housatonic River, both by road and railroad bridge. The following is a list of crossings of the Housatonic River in order of occurrence from the river mouth at Long Island Sound to its principal source streams in the Berkshire Mountains.
| Bridge | Route | Location | Built | Notes | Coordinates | |
|---|---|---|---|---|---|---|
| Rannapo Road | 42°03′31″N 73°20′34″W / 42.05861°N 73.34278°W | |||||
| Housatonic Railroad | 42°04′10″N 73°20′25″W / 42.06944°N 73.34028°W | |||||
 Route 7A
|
42°04′11″N 73°20′24″W / 42.06972°N 73.34000°W | |||||
| Green Bridge | Bridge Street | Great Barrington | Green pony truss bridge, 2 lanes | |||
| Cottage Street Bridge (closed) | Cottage Street | Great Barrington | Rustic pony truss bridge, closed to traffic, 2 lane, abandoned | |||
| Butternut Bridge | State Rd/Main Street | Great Barrington | Refurbished 2020/21 | Two lane red pony truss bridg | ||
| Division Street Bridge | Division Street | Vandeusenville | 2022 | Temporary 1-lane truss bridge, gray, to be replaced | ||
| Park Street Bridge | Park Street | Housatonic | 2017 | Two-lane beam bridge |
The following crossings refer to where the West branch of the Housatonic River splits, and the East branch begins:
The following crossings are along the west branch of the Housatonic River:
The following list contains Housatonic River crossings along its southwest branch:
