Motels -- Suddenly Last Summer
The ice cream truck in the beginning of the video and then later on is totally relevant to this theme. Martha Davis, who wrote the song, described the childhood memory of an ice cream truck driving around the neighborhood as the sun set earlier in the evening as the unmistakable sign that summer was ending.
I've always thought this was a very underrated 80s hit.
The Boys of Summer has some of the best lyrics of any song I know. The way he tells this girl that his love will outlast the other boys by comparing it to a tourist town long after the season is over is just genius, and it really paints a vivid picture in my mind like few other songs can.
And ones that are ostensibly set in the winter have more of a late fall feeling (brown leaves, gray skies) -- "A Hazy Shade of Winter," and "California Dreamin'."
“It’s amazing how many songs with “summer” in their title or their lyrics are really about the fall — or, more accurately, about the melancholy mood as summer fades to fall.”
I was thinking something very similar, I was about to post Frank Sinatra’s “Summer Wind” as the archetypal Autumn song but I thought people would think I was crazy posting a song with “summer” in the title as a great Autumn song.