From where I live, it would have to be the southern leg of I-684 leading to I-287. Might have on a bus on a field trip to NYC, but I’ve never driven it. I always use the Saw Mill when I head toward NYC and points southwest, and I’ll use the Hutch connection going to Long Island. That would be about 70 miles from me. Next closest is the Thruway between Exits 17 and 19, about 80 miles. The whole 17-21A stretch is out of the way. I’ve only driven 19-21A once driving from Lancaster PA to Lake George, but took US 209 as the hypotenuse of the 84/87 triangle between Port Jervis and Kingston.
MA 57 can be desolate, especially at night. I would take it as part of the backway home from Springfield if there was night construction on I-91 or I-84. The west end reminds me of how I-691 (then CT 66) used to end at Exit 4. You can see where it was meant to extend beyond MA 187. There is one EB Exit at MA 75 (creating a palindrome).