"Valparaiso in a Rowboat" by Zeke Hoskins is about Windsor, Ontario.

"Lonely Yukon Stars," my favorite Riders in the Sky song, is of course about the Yukon Territory.

Numerous Stringband songs I know or half-know are about places in Canada.

Here's one Stringband song I believe I know by heart. It's about the demise, in Whitehorse by arson in 1974, of two of the last sternwheelers on the Yukon River (you can read about this event, and see photos, here. I love everything about this song, but especially the small positive vignette Bob was able to pull out of this sad story:

THE CASCA AND THE WHITEHORSE BURNED DOWN
By Bob Bossin

We could smell the smoke just as soon as we awoke
On a ridge running east from town
I put the coffee on, a thermos took along
When the Casca and the Whitehorse burned down.

The city volunteers pumped water from the river
To try and hose the old boats down
But the old wood was so dry and the flames they rose so high
That the Casca and the Whitehorse burned down.

"Fire!" he cried. "Fire on the river!"
Muddy waters rollin' deep and brown
Old man callin' down along the river
When the Casca and the Whitehorse burned down.

Old Captain Jim O'Hara he was sittin' in a lawnchair
And damned if that old man didn't laugh.
He pointed to the smoke, a-rising from the stack
And said, "When did you last see that?"

Fifteen cord to Dawson and a hundred comin' back
Look down how those muddy waters roll
The churning paddlewheel raisin' rainbows in the wake
And hear that old steamwhistle blow.

Fireweed, the perfume of the smoke
Muddy waters rollin' deep and brown
Pink ladies down in Dawson all come out to watch the boats
When the Casca and the Whitehorse come down.