Sugarcube
My absolute favorite record for the transition from late summer to early fall is Yo La Tengo’s I Can Hear The Heart Beating As One. The affinity has to do with more than just the fact that there is an (excellent) song called “Autumn Sweater” on the album, but that surely doesn’t hurt. The guitars crackle like stepping on dead fallen leaves. There’s a whole section of this 2xLP where it sounds just like the cooling down on a hot summer night (complete with crickets chirping). You can almost see the lightning bugs flickering on and off.