Hello New England Lads, I am coming your way

So, its that time of the year again, when the beautiful leaves start to turn magnificent colors and you know yourselves, the New England states are the most colorful and charming! So, I will be making my little tranquil drive and would love to know which areas are good for visiting. I do want to visit some small towns and big towns, so would love some suggestions.
Even better, if any of you New England boys could email or private message me some ideas, Id love to make a little plan on where to visit.
A little question I have: How are you boys for travelling when there is a lady you would love to see, who is fairly close but not exactly in your town? Since you have cars, do you find it troublesome to travel a bit to see someone you like? Just a few things for me to consider. Thanks so much and hope to see you soon! Maybe as soon as this weekend!

Which months do you find yourselves slipping around on ice or having lots of snow to drive thru? Do you find New England winters to be harsh? I am in New York City, and we dont get very much snow and I always wondered how New England would be to visit in the winter. And which months can be the most harsh for weather. Any tips if I decide to make a winter visit?

If you're going to northern Maine, I'd stick with August.....

Im thinking Springfield, Hartford, Albany and maybe further north too. And Boston of course.

Knowing Pittsfield that seems very plausible.