Adolescence to ? (not all of us are parents):

The Gallery by Joni Mitchell
You're Gonna Lose That Girl by the Beatles
Silly Sisters by June Tabor and Maddy Prior (the whole album)
Sail Away Ladies by Odetta
Classic Scots Ballads by Ewan MacColl (the whole album)
My Son David by Jeannie Robertson
Who'll Stop the Rain by Creedence Clearwater Revival
American Pie by Don McClean
Winter and I by Carol Denney
Don't Think Twice It's Alright by Joan Baez

Later Years:

The Granmore Hare by Dick Gaughan
Lola by Swan Arcade
Will Ye Go to Flanders/MacCrimmon's Lament by Out of the Rain
Statesboro Blues by Chris Smither
Dimming of the Day by Richard Thompson
No More Fish, No Fishermen by Finest Kind
Who Built This House by Carol Denney
Enola Gay by Kate McDonnell
The Famous Flower of Serving Men by Martin Carthy
First We'll Take Manhattan by Leonard Cohen

Note: I'm following the conventions of this list by naming the performing artist rather than the author.

This was harder than I thought: typing one title makes me remember another. Then I get almost done and think of something vital I missed. I guess I'm not a top ten kind of a gal