Your descriptions are as eloquent as your painting is wonderful.

I live in California and just spent a week in Maine where my husband is from. Let me tell you, it was not even close to the height of winter and we were cold. We would run out to the car or in a shop in just maybe a sweater but if we were outside for any length of time it would get to me (and the kids) after just a few minutes. I was advised to do lots of layers rather than a SUPER heavy coat and that was perfect, but it required an intentional base layer meant to hold in warmth. I’m not an expert on cold like natives would be, but I am an expert at spending time in cold places as a person who lives in a warm place. Regardless of how you layer, you’re going to want a nice coat of some sort, nice warm boots, and some gloves. Our cold hands were the only part that really felt uncomfortable (and that was with gloves, just not good ones.)

I will also add that the clothes you purchase there (in Maine) were much warmer and thicker than what we could easily buy here at home. We did do LL Bean because our family is in Freeport, but even at Old Navy and such, the fabric was heavier overall, so you can certainly add to your wardrobe once you get there.