Before moving to Meredith we spent 15 years in the West Boston burbs (Maynard) and travelled regularly to visit my folks in Winchester, VA.
First time was via 95 - and that was the last time for that. After that we used 81 to Scranton and then 84 thru CT to the Mass Pike.
After a couple of unpleasant trips through CT in what should have been straightforward Winter weather we decided that it was worth the theoretical extra half-hour to catch 87 N off of 84 in NY and head up towards Albany and get on 90 there. 2 points worth noting: a) because of the difference in traffic, this detour is sometimes not any longer time-wise, and is a million times more relaxing, and b) I'd take Winter driving in Albany any day over CT.
So: 81 - 84 - 87 - 90 - 495 - 3N (pay the toll. 93 in MA is awful) - 93 - whatever you like from that point.
Good luck.
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