Moonlight in Vermont
Not much in the way of music has come out of this part of the world. I don't know how much really dynamic potential it has, given the climate, the lack of major cities, the ethnic composition and comparatively sober temperament of the population, but I am surprised there haven't been more pop bands at least of the slightly offbeat, depressive, dreamy-sounding type such as frequently comes out of the north of Britain. The people who try to take up music around here don't seem to identify real strongly with what they are, musically anyway; they want to connect with what they perceive to be going on of some kind of importance out in the Real America, which in musical matters is always assumed to be so much more interesting and advanced than here that there isn't even a sense of what a good "New England sound" would possibly be like. Whatever is the reason, songs do not flow naturally out of the patterns and habits of day to day life in these parts.
Though (according to the Internet) written by one guy from California and another from Ohio who came to Vermont while travelling with a puppet theater group, "Moonlight in Vermont" is a rare classic featuring the area. Though the song was written in 1943, the state still looks and feels like the winsome atmosphere evoked by both the lyrics and the tune. If one were to hear it when far away from home, and had spent any time there as a younger man, it would call up all those associations of youth and one's rawer, more hopeful self as experienced through this prism of nature quite beautifully I would think.
Another song that I have always found reminds me of the psychological atmosphere of this part of the world, winsomeness running up against the realities of the climate, the past-orientation of much of the actual geography of towns and routines of living that this still necessitates (which I also think accounts for the extreme popularity and identification with the game of baseball and the Red Sox in particular, compared to people living in more blatantly 21-st century regions) is the Neil Young song "Harvest Moon". I feel somewhat manipulated by it and suspect it isn't a very good song, but it does capture something in the mood of that end-of-fall time in a northern country, where you think you are, or must be, sad, but actually you are happy and optimistic, though this is not apparent to outsiders, which the record of your life, if you keep one, will demonstrate.
I chose to put the Sinatra version on the page here because it is famous, the video had some live action, and, as one of the commentators on Youtube put it "Frank owns this song". I like girl singers though, so I thought I would check some of them out. I found Jo Stafford, who is one of those singers you think isn't so good when you try to intellectualize about her, but then you don't get tired of hearing her versions of songs over and over, and prefer them almost unconsciously to ones you are sure are better. I used to have one of her records in college and I listened to it all the time. All the while I knew other guys were putting on Billie Holliday albums and drawing girls into their rooms and rendering them powerless to resist their advances by the elevated atmosphere; but I never liked Billie Holliday a tenth as much as Jo Stafford. She is like ice cream to me. Margaret Whiting did an early version of the song, which is also good.