The cool thing is the town is bought-in to the idea of being a destination for cyclists being the end of the Columbia Trail.
The initial parts of Nassau System were successful, an expansion was pitched, improvements, connections -
little pump track, flow trails. All with the blessing of the town (due to solid individual efforts)
It was all very cool, and in government glacial time frames, they are the exception. I think they started digging in 2013 (???)
@Jeffreywoliver - is there a documented history? The High Bridge website seems to be unmaintained
those are grade reversals for water management. Sometimes there is more water to deal with than others.