In Massachusetts, any snow before about Veteran's Day is very rare, but can be quite strong when it does happen.
Just before Halloween 2011, my current home of Tewksbury got about 5 inches of snow. Former home in Fitchburg got 17, and Ashburnham to the northwest got over 25. It was also 60+ degrees for about 10 straight days after and in Fitchburg I got a mere 20 inches of snow the rest of the year after.
Famously, a Baltimore Orioles World Series game in 1979 got snowed out on Columbus Day. Given how far south and how early that was, that one always fascinated me.
The Patriots also played a mid-October game in 2009 that had snow throughout. The Tennessee Titans were a complete mess dealing with it, and the Pats won 59-0.
The earliest I've seen snow in Massachusetts is October 10th (in 2000).