Every summer I mix a new "road" cd, but there are three songs that carry over onto each one:
"On The Road" - Carl Franzen
"A Big White House in Indiana" - Larry Groce
"I Hear America Singing" - Bob Gibson

"On the Road Again" by Tom Rush is a good road song especially if you are traveling up or down the east cost.

Favorite Road songs:

Pack Up Your Sorrows...Judy Collins

Uncle Pen...Ricky Scaggs

On the Road Again...Canned Heat

Early Morning Rain...Gordon Lightfoot

Are You Ashamed to Call Me Darl'n...Lonsome River Band

Anything by Mat d and the Profane Saints to get me past the city limit signs...especially "The Ghost of Huddie Ledbetter".

Some Vinnie James for the scenic spots, like "Summertime".

And just about everything from Jim Lauderdale or Wayne Hancock for the long, lonely stretches between dusk and dawn.

Favourite Road Songs -

Many a Long and Lonesome Highway - Rodney Crowell
Snowing on Raton - Townes Van Zandt but Rosalie Sorrells version
Interstate Blues - Jeff Talmadge
Road Too Long - Slaid Cleaves

One of my favorite road somgs is Long Way by Antje Duvekot. The song captures her wonder at discovering different parts of the country and its culture.

My son, who is into the folk sceen in Boston and has seen her often describes he this way:

Antje Duvekot - Long Way
Originally from Germany but living in the US since she was a teenager, Antje Duvekot became an
overnight sensation a few years ago with this song. It was played (and probably still is) on WERS (the
Emerson College station) maybe 10 times every morning. Her songs are simple and often unpolished but insightful and sometimes quite moving.

Antje is a master storyteller with her songs and one feels like one is beside her on this cross-countrty journey that takes her as the mood moves her, but with a longing for her friends left behind.

Paul Levin - Shaker Heights, Ohio

Come a Long Way - Michele Shocked- (And she never left LA!!!)
When I was a dinosaur-Trout Fishing in America - (It'll wake anyone else in the car in a hurry)
LA Freeway / Homegrown Tomatoe- Guy Clark
Choctaw Bingo - James McMurtry (It always reminds me of home being a transplanted Okie!)
Lyle Lovett's CD's are great too!

I dig the hell out of Dave Moore on the few road trips I've taken lately. Guy Davis too.

Willin by Little Feat and the whole of Hejira, also Don Juan's reckless daughter. But Isabelle still shouts "Arrrgh Joonie Miitchell" from the back seat. So lots of comedy.

She's really keen on Mr Slater's Parrot by the Bonzo Dog Doodah Band.