Classic Rock, Festival Highlights & Modern Anthems

Each of the four seasons can be characterized by a specific vibe when it comes to the music we have on repeat. Regardless of genre, seasonal playlists are entirely surmised of the feelings evoked by their respective seasons. Summer, for example, is characterized by the upbeat, jovial sounds of youth, where winter may signalize more of a melancholy feeling.

The transitional period between two seasons is also a gold mine for playlist curation, as one can draw from their two combined feelings. With fall on the horizon, and it will be here before we know it, Labor Day weekend is all about soaking up those last few drops of summer—and, of course, the ever-popular three-day weekend.

No matter how you’re spending your Labor Day—on a boat on a lake in the Midwest, at a festival on the coast, or at a blowout BBQ down south—music will undoubtedly be a crucial part of making it as relaxing and enjoyable as possible, and any Labor Day playlist would be incomplete without some combination of these three vibes.

Retro Labor Day Classics

Ever since the ’80s, there have been a handful of Americana and Heartland Rock legends who have become, and will continue to be, staples on Labor Day for years to come. Heartland Rock rose in popularity, at least in part, due to the way it resonates with working-class Americans, the very people for whom Labor Day exists.

First, and arguably foremost, is “Pink Houses” by John Mellencamp. The quintessential Labor Day song sees Mellencamp asking “Ain’t that America” in a way that is both critical of how labor is sometimes treated in the US, but still celebrates our country just the same. In addition to the lyrics, this song boasts a sound that is the perfect balance between summer and fall vibes.

Of course, one can’t discuss Heartland Rock on Labor Day without mentioning The Boss. Nearly every song on Bruce Springsteen’s Born In The U.S.A. would be a great addition to your Labor Day playlist, but the one that really sticks out is “Glory Days.” It’s the perfect juxtaposition between enjoying Labor Day now, and reminiscing on the Labor Days of your youth, too.

Ironically, one of the most notable lines of “Mary Jane’s Last Dance” is “I feel summer creepin’ in / and I’m tired of this town again,” but the sound still prompts the feelings of the end of summertime, too. I’d be remiss if I didn’t shout out another Petty track, “American Girl,” but similar to Springsteen, you really can’t go wrong with Petty on Labor Day.

Live Staples And Festival Highlights

If there’s one thing Labor Day Weekend never lacks, it’s amazing live music experiences. Dozens of festivals take place across the nation, along with a number of equally massive individual concert experiences to fill in the gaps.

One of the biggest festivals on the docket this weekend was EDM’s North Coast, celebrating their 15th anniversary this year nonetheless. Closing out night one of North Coast was none other than Chris Lake, whose “Toxic” samples “Poison” by Bill Bev DeVoe, and happens to be a smooth yet upbeat dance hit, perfect for your Labor Day playlist.

This Labor Day Weekend also saw some massive concerts, including Oasis, whose Live ’25 world tour features a two-night event at MetLife Stadium with support from Cage The Elephant and Cast. One hit that will surely grace the stage at MetLife this Labor Day is “Live Forever,” a pleasant, laid-back earworm that oozes end-of-summer nostalgia.

Perhaps the biggest festival of the weekend, however, is none other than the Jazz Aspen Snowmass (JAS) Labor Day Experience. Don’t be fooled, though—the JAS Labor Day Experience is far from a jazz festival, as evidenced by this year’s modern rock headliner, Imagine Dragons, whose “Bones” should fit nicely between Chris Lake’s EDM and Bruce Springsteen’s ’80s sentimentality.

Modern-Day Anthems

As much as Heartland Rock and electric live performances tend to dominate Labor Day, it’s the new-age folk rock anthems that tie everything together. No Labor Day playlist would be complete without the modern rockers who took Tom Petty’s influence, and are using that inspiration to light up the stages at the festivals of today.

Big Thief is the 21st century folk Americana band for 20th century fans of Creedence Clearwater Revival or Joni Mitchell. Their southern country and modern folk influences check all the boxes of nearly every major decade of contemporary music. Their track “Red Moon” is an upbeat, yet soft and easy track, perfect for any summer to fall transitional playlist.

The War On Drugs is dad rock if dad rock was a genre that was still in its defining phase. Lead vocalist Adam Granduciel has an inherently soothing voice, and on the band’s fifth album, I Don’t Live Here Anymore, they partnered with fellow modern rockers Lucius for the title track, creating an equal parts soothing and exciting end-of-August anthem.

Americana has certainly evolved in the last decade or so, with artists like Ethel Cain leading the charge. Though her sound does tend towards gothic dreampop, the third yet arguably most popular single from her breakout album, Preacher’s Daughter, “American Teenager,” is a nostalgic, upbeat, Heartland Rock-influenced reckoning with what it’s like to be, well, an American teenager.