Days like that should last and last and last…

I treat end-of-summer songs the way most people treat Christmas music.

There is an entire segment of the music industry that is built around the fact that, for at least a month at the end of every year, a significant percentage of the music-listening population only wants to hear holiday songs. It’s why Mariah Carey’s “All I Want for Christmas Is You” will have an annual stint atop of Billboard charts from now until the end of time, and why Spotify Wrapped cuts off streaming stats for its users around Halloween. The last six weeks of the year is holiday music season.

Well, for me, August is end-of-summer music season. I have an entire playlist of songs that I associate solely with the fading of Earth’s most glorious season. Most of those songs, just like Christmas carols, sound wildly out of place to me if I hear them at any other time of year. But play them for me in August, especially in those last two weeks before Labor Day, and my heart will ache with all the melancholy of watching another summer die.

No song on the planet captures the sweet, sad feeling of summer’s end better than Dashboard Confessional’s “Dusk and Summer,” and its perennial re-entry into my life has made it one of my most cherished songs of all time. To tell that story, I have to break with the typical mold of this essay series – most parts so far have focused in on one specific memory or period of time – and explain the evolution of my end-of-summer ritual, and how music came to be a core part of it.