Entertainment Music The Best Songs for Your Fall Road Trip Playlist Share PINTEREST Email Print DenisTangneyJr/Getty Images Entertainment Rock Music Pop Music Alternative Music Classical Music Country Music Folk Music Rap & Hip Hop Rhythm & Blues World Music Punk Music Heavy Metal Jazz Latin Music Oldies Learn More By Kim Knox Beckius is a Connecticut-based travel writer, author, photographer, and editor. our editorial process Kim Knox Beckius Updated June 19, 2020 As I was driving to the William Cullen Bryant Homestead in Cummington, Massachusetts, on a spectacular fall day, my iPod Shuffle played an apropos song: James Taylor's Country Road. I decided that instant I needed to research fall songs and create a fall playlist for all of my autumn trips. If you're planning to hit the highway on a New England fall foliage road trip this year, here are some suggested fall songs for your listening pleasure. I've selected an eclectic collection of classic New England and fall songs, contemporary tunes and a few songs that simply seem fitting for a fall driving soundtrack. I'd love it if you shared your favorite fall playlist songs, too (contact Kim)! Kim's Fall Songs Playlist 1. Indian Summer – Poco, from the CD Poco: The Ultimate Collection 2. Country Road - James Taylor, from the CD James Taylor: Greatest Hits 3. Change of Season - Hall & Oates, from the CD Change of Season 4. O New England – The Decemberists, from the CD single Always the Bridesmaid: Volume I 5. When Fall Comes to New England – Cheryl Wheeler, from the CD Driving Home 6. Weekend in New England – Barry Manilow, from the CD Barry Manilow Greatest Hits Volume II 7. Autumn Leaves – Nat King Cole, from the CD The Unforgettable Nat King Cole 8. True Colors - Cyndi Lauper, from the CD Twelve Deadly Cyns… And Then Some 9. Moonlight in Vermont - Willie Nelson, from the CD Stardust 10. Seasons Change – Expose, from the CD Exposure 11. When the Leaves Come Falling Down – Van Morrison, from the CD The Best of Van Morrison, Vol. 3 12. Boston – Augustana, from the CD All the Stars and Boulevards 13. Beautiful Sunday – Daniel Boone 14. Forever Autumn – The Moody Blues, from the CD Lovely to See You (Live) Fall Instrumental Selections If you'd prefer instrumental songs to accompany your fall ramblings, George Winston's Autumn album of New Age piano music would also be very appropriate. More Instrumental Songs for Fall 1. The First of Autumn – Enya, from the CD A Day Without Rain 2. Falling Leaves – Glen Miller Orchestra, from the CD Glen Miller 100th Anniversary: 75 Top Ten Hits 3. Falling Leaves – Mark Wesling, from the CD A Day of Music (Buy from the Artist) 4. Gently Raindrops Falling on Leaves – Daniel Kobialka, from the CD Pathless Journey