Isn’t it sung as if September isn’t over yet?
Here some good September songs to me.
Lies - Stan Rogers
Birches - Bill Morrissey
75 Septembers - Cheryl Wheeler
River - Bill Staines
To me Bill Staines songs are almost all good September songs.
September Songs:
They are the harvest songs you listen to on a sunny fall day of Indian summer. The ground is dry and cool enough to sit on while you watch birds feeding on cosmos seeds, or dusting on a dry patch of ground. You get to open those surprises that have grown all summer while you waited and labored. The bright orange pumpkins peek through the leaves now. The insect’s drone and thrum the air. The apples perfume the air as they sweeten enticing you to eat one. The birds will soon succumb to the cry of follow, follow, that blows on the wind. It’s the songs that make you want to follow, and to see new sights and places. You desire to follow the birds and the winds to warmer lands. Not now the sun is warm and you are tired. The songs carry you through daydreams and contemplations.
For me, it’s always been Don Henley’s “The Boys of Summer”: http://www.youtube.com/watch?v=kmoWIhMOjmg
The late great Sarah Vaughan’s September Song.
Me, too! Sept. 16. How about you?
Sinatra has an album devoted to this theme, “September of My Years,” with the following songs:
“The September of My Years” (Jimmy Van Heusen, Sammy Cahn)
“How Old Am I?” (Gordon Jenkins)
“Don’t Wait Too Long” (Sunny Skylar)
“It Gets Lonely Early” (Van Heusen, Cahn)
“This Is All I Ask” (Gordon Jenkins)
“Last Night When We Were Young” (Harold Arlen, E.Y. Harburg)
“The Man in the Looking Glass” (Bart Howard)
“It Was a Very Good Year” (Ervin Drake)
“When the Wind Was Green” (Henry Stinson)
“Hello, Young Lovers” (Richard Rodgers, Oscar Hammerstein II)
“I See It Now” (Alexander Wilder, William Engvick)
“Once Upon a Time” (Charles Strouse, Lee Adams)
“September Song” (Kurt Weill, Maxwell Anderson)
The lovely title song can be heard here.
There’s a sort of sweet melancholy in many of these songs. Reflective but not exactly sad.
As I am a big Jonathon Coulton evangalist, I have to add his Summer’s Over to the list, too:
(Coulton releases his music under a Creative Commons license; sharing lyrics in this context is a-ok.)
That’s one of the songs I first thought of.
After I thought about it, “April Come She Will” is a very apt September song, despite its title. Melancholy is a common element for these “Spetember songs,” huh?
the 8th, so I got first-day-of-school as a present every year. Yay! 
[note: this isn’t the YouTube video you meant to link to for this thread, is it? I’m guessing that’s meant for [thread=529626]this thread.[/thread]]