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Because sometimes the days between Thanksgiving and March 21 can seem very long and very dark.

• “February” by Dar Williams (but Joan Baez does a nice cover too)
• “The River” by Joni Mitchell and sung most melancholic by James Taylor and Robert Downey Jr. (surprising but true!)
• “Winter” by Tori Amos
• “Sister Winter”  by Sufjan Stevens: Honestly, all of his songs have a tinge of sadness about them but this one seems particularly so.
• “Have Yourself a Merry Little Christmas” originally sung by Judy Garland by covered nicely by James Taylor (he’s got the sad winter song thing covered)

Related posts:

1. 5 songs about rain because it just won’t stop
2. 5 songs of this summer from worst to best
3. 5 best hymns for the season