The Best New England Road Trip Playlist for Your Next Drive

Crank the windows down. The road north from Concord on I-89 cuts through some of the best scenery in New England, and there’s a song for every mile of it.

The playlist concept, as Yankee Magazine assembled it, pairs familiar sing-alongs with unexpected detours. Think of it less as a curated album and more as a glove-compartment mixtape: some fast, some slow, a few new, and the rest you already know by heart.

Start with “I-89” by folk supergroup I’m With Her. The band wrote the song after leaving that same highway to brave a Vermont byroad and promptly getting their vehicle stuck. Any driver who’s white-knuckled a rural shortcut in mud season will feel the refrain, “If there was another way out, I’d take it,” in their bones. The Get Up Kids follow with “Mass Pike,” a regret-soaked drive down I-90 where romance, not road conditions, causes all the damage. Two interstates, two very different kinds of stuck.

Then Donna Summer arrives. Boston’s disco queen, born in the Mission Hill neighborhood, never said what inspired “I Feel Love,” but the playlist suggests foliage season as a candidate. October light bouncing off the Deerfield River does strange things to people.

Ray LaMontagne, a New Hampshire native who’s lived across the region, contributes “Drive-in Movies,” a nostalgic track about summer nights watching films from a car. The source material doesn’t pin down which town he had in mind, which is part of the appeal. Pick your own drive-in and let the song settle over it.

The playlist gets specific fast. Judy Garland and Bing Crosby harmonize on “Connecticut,” calling it “spick and spanner than old Montana.” Local legend Dr. Westchesterson, in “(I’m From) Western Mass,” raps about everything west of Worcester and squeezes in what the playlist calls “the most bars ever rapped about the Big E.” That’s a genuine New England flex.

The Dropkick Murphys.

“I’m Shipping Up to Boston” doesn’t invite you to the city so much as shove you through the door. The Dropkick Murphys built a sound out of Southie rowdiness and Celtic punk fury, and this track is the fullest version of it. It sounds like a bar fight. In a good way, as the source puts it.

Boston the band, not the city, chips in with “Rock & Roll Band,” a track about playing dives and scraping gig money across New England. The lyric “Dancin’ in the streets of Hyannis” holds up as both a geographic reference and an actual weekend suggestion. Neil Diamond’s “Sweet Caroline” closes the Massachusetts portion with the inevitability of a ninth-inning stretch at Fenway Park.

“This list really captures how people actually move through New England,” a regional travel guide editor told a colleague of mine at a tourism conference in Portland last spring. “You’re not just driving through states, you’re driving through feelings tied to specific exits.”

That’s the thing about a road trip playlist built around real place names. I-89, the Mass Pike, Western Mass, Boston. You don’t need the map open when the songs are doing the geography for you. Pack the car early, skip the turnpike where you can, and let the White Mountains or the Berkshires or the Connecticut shoreline fill the gaps between tracks.