Housatonic Heritage offers Heritage Walks every year. And each year, the list of participating sites grows.
The walks (cycles, paddles, etc.) are free, guided interpretive tours to off-the-beaten-path (or hidden in plain site) historic, cultural, industrial, and natural sites in Berkshire County, MA, & Litchfield County, CT.
All happening over five weekends in September and October.
Take a look here.
https://housatonicheritage.org/heritage-experiences/heritage-walks/