I live in Massachusetts and I had to look it up. I figured it was maybe in the Berskshires somewhere--which I'm also not that familiar with but as it is no wonder I hadn't heard the name before. Any list like this is going to be a bit idiosyncratic but this is more random than most.

Bash Bish is scenic but it is way too crowded in the summer with NY tourists. Id recommend googling for other Western Mass trails a little rather from NY.

I grew up very near Bash Bish and–while always a popular local spot–it has really succumbed to the the instagram must-have-selfie phenomenon in recent years. There are thankfully plenty of other beautiful places nearby!