Ahhhh, this gets the storm chaser in me excited!
Rare, yes. But certainly not unprecidented.
For example on June 9th 1953 Worcester county had a
HUGE F-5 tornado that killed 94 people, it was one of the most powerful tornadoes on record. There's a terrific book on that tornado called "Tornado! 84 Minutes, 94 Lives" by John M. O'Toole which I highly recommend, especially if you want to read some truly incredible real-life tornado survival stories. I live in Massachusetts and have heard of few stories from people too.
There was also another monster F-4 that hit Great Barrington (far western MA) like fifteen years ago and killed three when it picked up a car and threw it a couple hundred feet into the woods, and personally I almost caught a small one on tape that went through Otis like 10 years ago but never caught up with it (probably lucky for me).
Also it depends on what you mean by "tornadoes all over the place", are you talking 2 to 4? Because that has happened, at least with small tornadoes.
Or are you talking about a "super outbreak" as they're called where there can be dozens over a multi-state region in a matter of hours? To the best of my knowledge that hasn't happened in the New England area, at least not yet.
So your scenario... either way it would be a very rare event, but definately possible, in fact we're probably due for something major. You could say any scenario is possible as recorded weather history (storms anyway) does not go that far back, it could be that freak storm systems of incredible destructive potential happen on timescales of like once every thousand years, and we simply haven't seen one yet.
Would a huge storm with tornadoes all over the place be strange for MA in the winter time? (specifically, Weston in Middlesex Co.). I'm trying to formulate a character reaction; the tornadoes are plentiful (several sightings of touchdowns, an F5 that plows these people's neighborhood).
THanks.
*sorry the title should read "Tornadoes IN MA"
technical blunder...