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Subscribe and listen to Holler's Best Country Songs For Fall Playlist above.
Grab your favorite sweater and stock up on the bourbon - autumn has officially arrived! Have no fear though, we’ll keep you warm with a list to celebrate the changing of the seasons.
Filled with autumnal tunes to be grateful, nostalgic and a little bit heartbroken to, here's Holler's list of 20 of the Best Country Songs for Fall.
One of Emerson’s best performances to date. A striking ode to his Choctaw-Apache heritage that demonstrates the sheer power of music. His stirring lyrics are matched by the soaring rock arrangement. It burns as bright as any bonfire flame.
Returning to her roots, Musgraves' soothing vocals shine as she explores the process of change within herself. A memorable reminder to reflect and observe as the leaves start to fall around us all.
Is there a chill in the air? From the opening, Booth conjures the first few moments of seasonal change with stirring vocals that capture the unshakeable sadness of leaving a love behind. “You grew me like a flower/I loved you like the sun/You ran like water/ I could never get enough,” she sings, remembering the warmth of that first unrequited connection even while knowing that it would never last.
A standout from Adeem the Artist’s acclaimed 2024 album Anniversary, ‘Rotations’ expertly embodies the ever changing seasons of parenthood. It’s a stunning performance that while at times somber serves more as a universal celebration of the bond between a parent and child. A perfect pairing with a cup of coffee as the kids head off to the bus stop for the new school year.
Fall is a gift to songwriters it seems. Max D. Barnes and Skip Ewing makes use of every autumnal metaphor there is in this country power ballad from Lorrie Morgan's 1991 album, Something in Red. Morgan plays the quintessential country stoic as everything begins to change all around her including the leaves and the warm weather.
Everyone from Swiss post-industrialists The Young Gods to Echo & The Bunnymen's Ian McCulloch and Frank Sinatra have taken on the classic Kurt Weill America Standard over the years, but Willie Nelson's version on his 1978 album Stardust is the one that really leans into the season.
The lyrics deal with an older man who looks back on his younger days from the vantage point of being in the "September" of his life. Nelson omits most of the verses and bridges of the original and dives straight into the guts of the song with a vocal that feels suitably wistful and worldly.
Taken from Zach Bryan's 2020 Quiet, Heavy Dreams EP, 'November Air' feels as stark and desolate as the encroaching Winter landscape as Bryan reminisces bitter sweetly about the past. The seasons change and the crisp November air reminds him of the fleeting nature of our own days, as he reflects poetically on a parent in their old age whose children have grown up and moved away.
"Two kids 'bout twenty-three and the sun sets you'll never see / You were yellin' 'Supper' from the yard," he sings in the second verse. "And they grew old and sailed away, called you on phones from far away / Wrote you novels on postcards / And all you ever wanted was to see your children fly / Maybe one day they're stars / But there ain't no leavin' this small town this evenin' / You can't even drive your own car."
For those of you that don't live in Vermont, "Stick Season" refers to a particular time between the autumn and winter.
This monster viral hit is set in that specific time of year that typically starts as soon as the leaves fall down and lasts from roughly mid-October to the beginning of December.
Serving as both the lead single and the title track for his third studio album, Noah Kahan’s 'Stick Season' has become one of his most well loved songs since it was released in July 2022.
“It’s definitely a song about, you know, the time in Vermont — stick season — when all the leaves are off the trees," Noah Kahan told Genius. "It’s a term that was used by some of the older folks in the town I grew up in to describe this really miserable time of year when it’s just kind of gray and cold, and there’s no snow yet and the kind of beauty of the foliage is done."
"And I love Vermont, but it's the season of the sticks," he sings. "And I saw your mom, she forgot that I existed / And it's half my fault, but I just like to play the victim / I'll drink alcohol 'til my friends come home for Christmas."
This Luke Bryan and Rodney Clawson cut from 2011's Tailgates & Tanlines finds finds the Georgia star celebrating the farming community back home that he grew up a part of.
Luke's songs like 'Rain Is a Good Thing' and 'Here's To The Farmer' have always reminded his fans where his agricultural roots lie, and on Tailgates & Tanlines, he made sure to include a couple for them.
"Songs like 'Muckalee Creek Water' and 'Harvest Time' were written from growing up in my hometown," he said. "I played 'Harvest Time' for some farmer buddies of mine back home and, man, a big ol' tear welled up in their eyes."
In this song from John Prine's last album before his untimely death in 2020, The Tree of Forgiveness, the changing of the seasons offers the promise of renewal as well as a time for reflection on what's been lost to progress.
Co-written with Pat McLaughlin, 'Summer’s End' was nominated for Best American Roots Song at the 60th annual Grammy Awards.
John Prine enlisted documentary filmmakers Elaine McMillion Sheldon and Kerrin Sheldon, best known for the Academy Award-nominated Heroin(e), to make the video for 'Summer's End' and they focused on a storyline about a grandparent bringing up his granddaughter after her parents have died from a drug overdose.
In Appalachia and other areas affected by the opioid crisis, this grandparent-raising-grandchildren is a common family dynamic.
“The opioid crisis is tearing American families apart,” John Prine wrote in a press release upon the video release. “I love what Elaine and Kerrin have done with my song for this video. I hope a lot of people see it.”
The transition from summer to fall in a beach town is nothing short of tragic; the sun fading into the distance as the landscape braces for the cold.
Bruce Springsteen’s gut-wrenching lyric is stripped back here and reinterpreted through Mercy Bell's nuanced vocal. Through it, Bell presents a deeper understanding of change with the hope of rebirth.
The changing of the seasons in Maine provides a perfect background for this apt statement about the end of a relationship.
Trunzo’s gritty and superbly honest approach is less about heartbreak and more about raw acceptance.
The former opening act and backup singers to Johnny Cash were famous for applying gospel-infused harmonies into country music.
Alongside this clever lyric, the layered vocals demonstrate such a heartfelt yearning that must only be heard while watching the first fallen leaves.
With lines like “when the icy winds blow through you / remember that it’s me who feels the cold most of all”, you’ll be hard-pressed to not feel the utter heartbreak yourself.
Reba McEntire delivers a tear-inducing vocal that will have you shaking your fist at this louse in New England.
The title track to Whitter’s superb 2022 album is an authentic testament to the bond of community.
A seasoned appreciation of individuals and spaces that shape and guide our lives. It's a reminder to give those close to you a call during this season.
Even a consummate gentleman like Johnson likes to have a rip-roaring good time. There's no pause for post-Summer sadness during this celebration of the colder months. Pull on your sweater, put another log on the fire, and get downright cozy.
When Strait’s honey-coated voice lingers into the chorus, you’ll feel the need to pour an extra shot of bourbon into your hot toddy. Who in their right mind would ever think of leaving the King of Country?
On his 1975 debut Old No. 1, Clark provided this tender but forthright cut about weathering any storm under the protection of a steadfast relationship. It’s a lyrical master class and one of a million reasons why he remains so beloved.
Ballerini always writes from a space of vulnerability and lived experience.
This nostalgic but universal reflection on her hometown will have you thinking back with a smile to those moments when your world revolved around Friday night football games.
Sure, it has one of the most iconic references to a scarf ever. Yet what is outstanding about the original 10-minute version is the precision of Swift’s craft.
The accompanying short film, while a welcome addition, wasn't needed with this strong imagery of lost love. Cozy up with a blanket and let her break you like a promise.