Well, I certainly wasn’t driving there from MA, but I did commute 25 mi (one way… occasionally 50 mi one way) to Lancaster daily for over a year and I never felt like roads were that bad, but I had AWD and good tires. Can’t speak for the highway conditions, as I wasn’t driving the direction that you’ll be coming from, but I did have to go through Randolph (or on my longer commute days, though the Notch) which always was much colder/getting hammered with worse weather.

If you’re worried, get decent snow tires put on. Worth it for the peace of mind!