You can see vestiges of history along trail points or go into the local towns to see them.
There are multiple routes, including one that falls east to west and another that is more north to south You can use the trail to take a walkable and, in parts of the trail, a bikeable path to other towns. This airline trail extends for a number of miles across Northwestern CT and much like other notable trails such as the High Line and Tow Path, it follows old rail lines and paths that were much more busy in earlier periods of time.