How many miles from NY to Great Barrington?

Answer 1

It's 125 miles taking this route (via the Taconic):

1. Take the TACONIC STATE PARKWAY - NORTH (towards ALBANY), from New York City, to the exit for ROUTE 23 towards CLAVERACK and HILLSDALE. Take the exit, and then turn right off the exit ramp onto ROUTE 23 - EAST towards HILLSDALE.
2. Take ROUTE 23 - EAST to Great Barrington, Mass.

Alternatively, you can take I-87 THRUWAY (toll road) - NORTH (crossing the Hudson River via the TAPPAN ZEE BRIDGE (toll)) to ROUTE 23 off EXIT 21, and then take ROUTE 23 - EAST from there. This route is longer (160 miles), but it may be better if you want to avoid the Taconic.