Play of the Land: A New England Road Trip Playlist

This New England road trip playlist pairs familiar sing-alongs with a few unexpected detours—some fast, some slow, a few are new, but the rest you know. Don’t see your favorite? Share your top tunes in the comments below.

Play of the Land: A New England Road Trip Playlist

“I-89”

Anyone who frequents the long road from Concord, New Hampshire, to Burlington, Vermont, may well sympathize with the refrain, “If there was another way out, I’d take it.” Folk supergroup I’m With Her penned the song after exiting the highway to brave a Vermont byroad … and getting themselves stuck.

“Mass Pike” – The Get Up Kids

Another song about an iconic New England interstate, this one by The Get Up Kids, describing a regret-filled drive on I-90. (In this case, romance is to blame, not the road.)

“I Feel Love” – Donna Summer

Time to bounce back with this dance-floor classic by Boston’s disco queen, Donna Summer. She never said who or what inspired this ecstatic outpouring of emotion, but we’d like to believe it was foliage season.

“Drive-in Movies” – Ray LaMontagne

New Hampshire native Ray LaMontagne has lived all across New England. It’s not clear which town he’s referencing in his nostalgic song about youthful summers watching movies from his car, so just assume it’s about the drive-in closest to you and enjoy the evening.

“Connecticut” – Judy Garland and Bing Crosby

Judy Garland and Bing Crosby sing a serenade to the “land of dreams and moonlit streams.” Connecticut has never received a more loving testimonial. “It’s spick and spanner / than old Montana”—yes indeed!

“(I’m From) Western Mass” – Dr. Westchesterson

In another ode to an overlooked homeland, local legend Dr. Westchesterson describes his love of everything west of Worcester. It features easily the most bars ever rapped about the Big E.

“I’m Shipping Up to Boston” – Dropkick Murphys

No one has captured the defiant, rough-around-the-edges nature of Boston better than the Dropkick Murphys. This song sounds like a bar fight, but in a good way.

“Rock & Roll Band” – Boston

This Boston classic about scraping by and playing gigs around New England captures the essence of being a struggling musician. Also, the lyric “Dancin’ in the streets of Hyannis” is a solid suggestion for a good night out.

“Sweet Caroline” – Neil Diamond

The anthem of Red Sox Nation, Neil Diamond’s classic is required to appear on this list by Massachusetts state law.

“Rhode Island Is Famous for You” – Erin McKeown

We end with a love song written about a girl from the Ocean State. Erin McKeown’s modern recording of this Broadway hit tells us that while bigger states might be known for their lobsters, peaches, and wheat, “You come from Rhode Island / Don’t let them ride Rhode Island / It’s famous for you!”

What songs would you want to cue up for a New England road trip? Let us know in the comments below.

This feature was originally published as “Play of the Land” in the May/June 2026 issue of Yankee.

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Justin Shatwell

Justin Shatwell is a longtime contributor to Yankee Magazine whose work explores the unique history, culture, and art that sets New England apart from the rest of the world. His article, The Memory Keeper (March/April 2011 issue), was named a finalist for profile of the year by the City and Regional Magazine Association.

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