Graphic - The Best Country Winter Songs

The Best Country Winter Songs

Ah, wintertime! The nights are long, the air is cold and we're all drinking too much Bailey's. We know that country music loves Christmas, but we've put together a playlist of 50 songs for all the chilly winter months surrounding it too. Stay snuggly, y'all! 

1. Merle Haggard - If We Make It Through December

5. Bill Monroe & His Blue Grass Boys - Footprints in the Snow

6. Melissa Carper - The Stars Are Aligned

7. Tyler Childers - Two Coats (Hallelujah Version)

10. Joy Oladokun, Chris Stapleton - Sweet Symphony 

12. Kris Kristofferson - Jesus Was a Capricorn (Owed to John Prine)

18. Johnny Cash - When it's Springtime in Alaska (It's Forty Below)

20. The Avett Brothers - Winter in My Heart

22. Carrie Underwood - Jesus, Take the Wheel

24. Marty Haggard - Shelley's Winter Love 

27. Dick Curless - A Tombstone Every Mile

29. Gordon Lightfoot - Song for a Winter's Night

30. Colter Wall - Thirteen Silver Dollars

36. Micky & The Motorcars - Rock Springs to Cheyenne

38. Guy Clark - Like a Coat from the Cold 

44. Glen Campbell - Cold December (In Your Heart) 

45. Iris Dement - Easy's Gettin' Harder Every Day

47. Don Williams - We've Got a Good Fire Goin'

48. Waylon Jennings, Jessi Colter - Storms Never Last

50. Phoebe Bridgers - If We Make it Through December 

Listen and subscribe to Holler's The Best Country Winter Songs playlist above. For more winter goodness, see below: 

A playlist of some of 50 of the best country songs for winter from Holler. 

Playlist

Featuring Merle Haggard, Melissa Carper, Zac Brown Band, Tammy Wynette and more

Country Winter Songs Playlist | Holler

Ciara Bains is a music journalist, radio host and musician from London, currently working as the Assistant Editor of Holler. She's a lover of all things disco, rock and roll and cosmic country. 

Ciara

Ciara author page 2022

Hailing from Castlewood, Virginia, 49 Winchester have always sought to incorporate the conflicting impulses of both longing for home and longing for the road into their music. Over the course of their four studio albums, the eight-piece band’s Appalachian folk has gradually blossomed into a rockier and more rough-around-the-edges sound.

49 Winchester have patiently built a loyal following over the course of their three independently released albums, which began back in 2014 with their self-titled debut release. This was followed by 

 in 2018, before the trio was completed by 

The band’s mercurial, definition-defying style caught the attention of Nashville’s go-to label for Americana and alt-country music, New West Records.

In 2022, 49 Winchester released their first album with New West, 

. the project received far-reaching acclaim, and served as a celebration of the band’s roots in Virginia.

The playful artwork depicts a coal miner, embodying 49 Winchester’s continued determination to pay homage to the blue collar traditions that have long formed the backbone of country music, as epitomised on ‘Hillbilly Daydream’.

elevated 49 Winchester from regional heroes to national prodigies. Various outlets championed the group for their eclectic mix of influences, with Holler naming the 2022 album as one of its Albums of the Year.

In 2023, 49 Winchester are set to embark on a hotly anticipated tour across the US, which will see them playing in Tennessee, Arizona and more.

49 Winchester

Artist - 49 Winchester

49 Winchester: News, Songs & Reviews | Holler

Singer/songwriter and multi-instrumentalist Allison Russell was born in Montreal, where music became an outlet to escape her troubled home. 

From that early interest, Russell joined the Canadian roots act Po'Girl in the early aughts. 

Eventually, she began collaborating with her future husband, Chicago-based singer/songwriter J.T. Nero, on his project mountains/forests until the pair eventually formed their own duo, Birds of Chicago, in 2012. 

They released several albums together until Birds of Chicago went on indefinite hiatus in 2021, as Russell turned her attention to her solo career with the release of her debut solo album 

Russell is also a member of Our Native Daughters, alongside Rhiannon Giddens, Amythyst Kiah and Leyla McCalla. The group released their debut album, 

Allison

Artist - Allison Russell 2

Allison Russell: News, Songs & Reviews | Holler

Amanda

Artist - Amanda Shires 2

Artist - Amanda Shires 1

Amanda Shires: News, Songs & Reviews | Holler

Amythyst

Artist - Amythyst Kiah 2

Amythyst Kiah: News, Songs & Reviews | Holler

Ashley Monroe began singing at a young age - even winning a talent contest at age 11. But it would take a few more years before she brought her talent to Nashville. 

Once she relocated to Music City, she landed a songwriting publishing deal that eventually led to a record deal with Sony Music. Her debut album 

 was ready to go, but her singles weren't charting as well as the label wanted, so they delayed and eventually pulled the plug altogether. 

 to digital retailers in 2009 - following it up with her self-titled EP the same year. Her emotionally driven, pop-country sound caught the attention of Warner Bros. Nashville, who signed Monroe and released her sophomore album 

 in 2013. Grand Ole Opry staple and legendary singer/songwriter Vince Gill produced it. 

, came out in 2015 and was nominated for Best Country Album at the Grammys. Three years later, after giving birth to her son, Monroe released her fourth album 

 in 2018. This time, Dave Cobb served as producer. 

Besides her solo work, Monroe is a member of the supergroup Pistol Annies with Miranda Lambert and Angaleena Presley. They released the albums 

 on 2018. The latter was nominated for Best Country Album at the Grammys. 

In 2021, Monroe released her fourth album 

Ashley

Artist - Ashley Monroe 1

Ashley Monroe: News, Songs & Reviews | Holler

Ashley McBryde didn't wait for the Nashville majors to back her talent. She self-released her first album in 2006, before moving to Music City to focus exclusively on writing and performing country music. 

In her first few years in Nashville, McBryde won the Country Showdown in 2009 and 2010. 

She continued touring behind her music, and eventually released the EP 

 in 2016. One year later, Warner Bros. Records in Nashville released her single 'A Little Dive Bar in Dahlonega'. 

McBryde co-wrote the song with Nicolette Hayford and Jesse Rice. It's about having the worst day but making the best of it. The song garnered critical attention, including from 

which named it as one of the 54 Best Songs of the Year. 

The single ended up on McBryde's 2018 debut studio album 

. Thanks to the popularity and critical success of the album, McBryde was named Female Vocalist of the Year at the ACMs and New Artist of the Year at the CMAs in 2019. Her debut album also earned a Best Country Album nomination at the Grammys. 

In 2020, she released her sophomore album 

. Once again, it was nominated for Best Country Album at the Grammys.

Artist - Ashley McBryde 1

Ashley McBryde: News, Songs & Reviews | Holler

Given that BRELAND grew up surrounded by gospel music — thanks to his minister parents — it would make sense that his career might trend in that direction. 

But instead he's developed a country sound that integrates elements of trap, hip-hop R&B and soul. Critics call it "country-trap", but BRELAND calls it "cross country". 

After growing up in New Jersey, BRELAND attended Georgetown University, where he performed in an a cappella group and worked on writing his own music. He moved to Atlanta after graduating and learned how to engineer, sharing the tracks he produced on social media. 

Those platforms helped BRELAND amass a following and a serious number of streams, all of which led to a record deal with Bad Realm Records/Atlantic Records. 

Following an eclectic self-titled EP in 2020, BRELAND put out the sobering and emotionally raw 

 EP, which he released in response to the Black Lives Matter protests that spread across the US that summer. 

In 2022, BRELAND released his debut album, 

, which featured collaborations with Thomas Rhett, Keith Urban, Ingrid Andress and more. The project's name captured the sonic mercuriality that has made BRELAND one of the most exciting new voices in country music. 

BRELAND

Artist - Breland 

Breland: News, Songs & Reviews | Holler

 EP in June 2022, it became the biggest streaming country debut of all time. Zimmerman also became one of just three country artists to earn over a million streams on each track during street week alone. The other two artists? None other than Luke Combs and Zach Bryan.

It’s sometimes difficult to believe that Bailey Zimmerman is still in his early twenties, and that he’s only been releasing music since 2021. In the space of just over a year, Zimmerman has enjoyed an ascent that has felt so meteoric, that he seems to have already transcended the labels of ‘prodigy’ and ‘prospect’.

‘Fall in Love’, one of the highlights from his 2022 EP, became his first Country Radio No. 1 in December. The single serves as the perfect encapsulation of what makes Zimmerman such a threat. It has the signature rasp and heart-wrenching intensity that pervades much of the project, but - crucially - it is packaged up with a pop-leaning production style that makes it ideal for Country Radio.

The result is a sound that simultaneously straddles both the mainstream and the outer edges of the modern country landscape. Part of Zimmerman’s ability to infiltrate both markets can be traced back to his blue collar roots, having grown up working on a gas pipeline.

In 2023, Zimmerman is joining Morgan Wallen on his blockbuster 

world tour. Zimmerman has previously cited Wallen as a mentor, with the Sneedville native having even co-written ‘Trainwreck’ from the 

When he heads out on the road with Morgan Wallen, Zimmerman will receive a first-hand glimpse into what it takes to become one of the biggest country stars on the planet. Given how emphatic Zimmerman’s emergence has been so far, few would be surprised to see him unveil his own world tour this time next year.

Bailey

Artist - Bailey Zimmerman 5

Bailey Zimmerman: News, Songs & Reviews | Holler

Country music star Blake Shelton learned to play the guitar as a young boy and took that talent to Nashville at age 17. He worked in and around the music industry, before eventually landing a record deal in 2001. 

Shelton released his first single 'Austin' that same year. It went to the top spot on 

's Hot Country Songs chart (formerly known as Hot Country Singles & Tracks). 

He released his self-titled debut that year as well, beginning a steady output of LPs that have accumulated to make him one of the most successful male country artists of his time. They include 2003's 

In between those albums, Shelton also released the 2012 Christmas album 

, Shelton accrued 17 consecutive number one country singles. 

Thanks to his impressive catalogue, Shelton was inducted into the Grand Ole Opry in 2010. The honor followed a serious number of industry accolades, including CMA, ACM and CMT Awards. Shelton won Male Vocalist of the Year at the CMAs five consecutive years, between 2010 and 2014. 

Since 2011, Shelton has served as a coach on NBC's 

. Thanks to his presence on the musical competition series as well as his music, Shelton made the cover of 

's Sexiest Man Alive issue in 2017. He became the first country music artist to achieve that title. 

Blake

Artist - Blake Shelton

Blake Shelton: News, Songs & Reviews | Holler

Artist - Bob Dylan

Bob Dylan: News, Songs & Reviews | Holler

Across an incredible catalogue of work, Americana singer/songwriter Brandi Carlile has written perceiving and perceptive songs. The Pacific Northwest native learned how to sing and play guitar and piano during her early years, translating those talents into a remarkable storytelling ability. 

Carlile released her self-titled debut album in 2006. But it was her 2007 sophomore album The Story — produced by T Bone Burnett — that began garnering more attention for her music. She turned to famed producer Rick Rubin for her 2009 album Give Up the Ghost.

Both her 2016 and 2019 albums – The Firewatcher’s Daughter and By the Way, I Forgive You – won Grammys for Best Americana Album. 

Outside of working on her own music, Carlile co-produced Tanya Tucker’s 2019 album While I’m Livin’ with Shooter Jennings. The moment was milestone, as Carlile had taught herself to sing by listening to Tucker and Patsy Cline.

She also performs as part of the supergroup The Highwomen, alongside Maren Morris, Amanda Shires and Natalie Hemby. Their song ‘Crowded Table’ won the 2020 Grammy for Best Country Song. In 2021, Carlile released her autobiography Broken Horses: A Memoir.

Carlile is out and proud. In 2008, she co-founded the Looking Out Foundation with the Hanseroth Twins, who she used to play in Seattle with as a young performer. It addresses multiple needs, and $1 from every concert ticket Carlile sells goes back to the non-profit. 

Brandi

Artist - Brandi Carlile 3

Brandi Carlile: News, Songs & Reviews | Holler

Brandy

Artist - Brandy Clark 2

Artist - Brandy Clark 1

Brandi Clark: News, Songs & Reviews | Holler

Brett Eldredge may have grown up singing jazzy vocal numbers by the likes of Frank Sinatra and other iconic crooners, but it’s country where he’s found his home.

Eldredge released his debut album Bring You Back in 2013, introducing listeners to his soulful baritone voice and earning three big hits. The singles ‘Don’t Ya’, ‘Mean to Me’, and ‘Beat of the Music’ topped the Country Airplay charts. 

Those early commercial successes translated into a CMA Award for New Artist of the Year in 2014.

His sophomore album, named after his home state of Illinois, came in 2015, and Eldredge followed it with the Christmas album Glow one year later. 

But Eldredge hasn’t left his past behind entirely. He regularly covers Sinatra and even told Rolling Stone that he’d love to record a covers album one day.

Eldredge’s fifth studio album, Sunday Drive, was released in 2020.

Brett

Artist - Brett Eldredge 1

Brett Eldredge: News, Songs & Reviews | Holler

Baltimore-born singer/songwriter Brittney Spencer grew up singing in church choir, a gospel foundation that has leant itself to the country music she's since crafted. 

Although she studied classical voice as a young girl, in the hopes of attending George Washington Carver Center for Arts and Technology, it was ultimately country that most entranced her. At age 15, a friend introduced her to the genre.  

Spencer moved to Nashville in 2013, where she began singing backing vocals for Carrie Underwood and Christopher Cross, among other artists. All the while, though, she kept writing her own songs and in 2020 she released her debut EP 

Her music garnered praise and led to her Grand Ole Opry debut in May 2021. Spencer has also been named to CMT’s Next Women of Country class of 2021. 

Brittney

Artist - Brittney Spencer 3

Brittney Spencer: News, Songs & Reviews | Holler

The country duo Brothers Osborne – John (guitar) and T.J. (vocals) – grew up playing music with their family, but that almost didn’t translate to a professional career. 

They both landed in Nashville after graduating high school two years apart, but they pursued other projects in an attempt to develop solo careers. But their power ultimately lay in playing together, and eventually they began performing as a duo at some of Nashville’s smaller venues. 

That push drew the attention of EMI Records Nashville, which signed John and T.J. in 2012. With that opportunity, they continued performing, releasing singles and recording a self-titled EP in 2014, all of which lead to their debut album Pawn Shop in 2016 and two big accolades. Thanks to John’s electrifying guitar playing and T.J.’s growling baritone, Brothers Osborne was named Vocal Duo of the Year by the Academy of Country Music and the Country Music Association in 2016 and 2017.

Brothers Osborne followed their early critical success with 2018’s Port Saint Joe and 2020’s Skeletons, albums which showcased their penchant for blurring country with southern rock. 

In 2021, T.J. made headlines when he opened up to TIME Magazine about being gay. The announcement made him the first country artist signed to a major label to come out. 

Brothers Osborne

Artist - Brothers Osborne 1

Brothers Osborne: News, Songs & Reviews | Holler

Artist - Cam 6

Artist - Cam 7 

Artist - Cam 1 

Artist - Cam 4 

Artist - Cam 2 

Artist - Cam 3 

Album - Cam - The Otherside 

Cam: News, Songs & Reviews | Holler

Carly 

Artist - Carly Pearce 1 

Carly Pearce: News, Songs & Reviews | Holler

Carrie Underwood’s career might’ve started much earlier had things gone a different way. At age 14, she auditioned for Capitol Records in Nashville. The label was going to offer her a contract, but that deal fell through when they changed management.

Underwood returned to Oklahoma, finished high school and later graduated from Northeastern State University. Things took a turn for the singer in 2004, when she auditioned for American Idol. Despite a shy start on the show, she would go on to become the season four winner, with a powerful voice that enraptured audiences around the globe.

But not every American Idol winner goes on to make such a big splash. Underwood’s first official single ‘Inside Your Heaven’ landed at the top spot on Billboard’s Hot 100 list, making her the first country artist to debut at number one. 

She released her debut album Some Hearts in 2005 and by 2006 she’d earned the Top Female Vocalist of the Year at the CMAs and ACM Awards. Her second album Carnival Ride arrived in 2007, the same year she won Best New Artist at the Grammys. 

Given Underwood’s popularity in country music, she began co-hosting the CMA Awards with country singer Brad Paisley, serving that role for 12 years. As she continued releasing new music, Underwood also starred as Maria in NBC’s live version of The Sound of Music.

When she released her fifth studio album Storyteller in 2015, Underwood became the first country artist who debuted all of her albums at either the first or second spot on the Billboard 200. 

In addition to her commercial success, which includes major headlining tours, and ongoing critical acclaim, Underwood has won several Grammys for her music. In 2020, she published her first book, Find Your Path, and released her eighth studio album My Savior in 2021.

Head here for a definitive list of Carrie Underwood's best songs.

Carrie

Artist - Carrie Underwood 3

Carrie Underwood: News, Songs & Reviews | Holler

Charles Wesley Godwin’s rustic imagery and traditional-leaning Americana sound has spawned comparisons with contemporaries such as Tyler Childers. While this assessment is an oversimplification, there is a notable similarity in the way that Godwin does not make any attempt to meet the listener where they are; if they want to enjoy the music, they’ll have to follow Godwin on a rocky trail through his Appalachian soundscape and into an entirely unique world full of enchanting characters.

Although he pointedly refuses to pander to mainstream impulses, the palette with which Godwin paints is nonetheless easy on the eye, and proves accessible to cosmic-country die-hards and boyfriend-country flag-bearers alike.

, was met with resounding acclaim, as the West Virginia native crafted a sound that felt expansive and cinematic, while at the same time being lucidly tuned-in to the details and specificities of the subject matter.

The project stood largely as an ode to his Morgantown roots, and Godwin maintained his charmingly grounded sensibilities throughout his follow-up 2021 album, 

. However, his 2021 offering widened the canvas and tested out new territory - both thematically and sonically.

The driving force that underpins Charles Wesley Godwin’s musical mission statement - and what many would argue should be at the heart of all country music - is a love of timeless storytelling. The listener meets a host of bewitching characters throughout Godwin’s discography, from the tragic tale of Claire, the mayor’s daughter, in ‘Cranes of Potter’, to the embattled protagonist of ‘Seneca Creek’.

Godwin continues to bring the soft, Autumnal glow of his warm melodies and wistful lap steel guitar to crowds across the US, having recently finished a hugely successful tour supporting fellow country-folk progressive, Zach Bryan.

Charles Wesley

Artist - Charles Wesley Godwin 2

Charles Wesley Godwin: News, Songs & Reviews | Holler

Charley Pride taught himself to play guitar as a young boy, but his heart seemed set on baseball. Pride pitched for various teams in the Negro League, in the 1950s, before being traded to the minors. 

Eventually, he ended up playing for a semipro team in Helena, Montana. That coach heard his singing ability and asked him to perform for a few minutes before each game in order to increase attendance. 

Pride cut a few demos at Sun Studios in Memphis, which ended up in the hands of RCA Records' Chet Atkins, who signed Pride, though publicizing him as a black artist singing country music remained a point of contention. 

Pride released a number of singles, but it was his third, "Just Between You and Me", that garnered him success. It reached the top ten on the Hot Country Songs chart in 1967 and was nominated for a Grammy. That same year, Pride became the second black artist to perform at the Grand Ole Opry - after DeFord Bailey. 

Pride's music continued charting, but it was his 1971 single "Kiss an Angel Good Mornin'" that became his biggest hit. It stayed at the top spot on the country charts for five weeks and even made it crossed over to the top-40 pop singles chart. 

In 1971, Pride was named Entertainer of the Year at the CMAs. 

Throughout the 1980s and 1990s, Pride continued touring and releasing hit singles. In 1994, he released his biography 

. In 1997, he had a tumor removed from his vocal cords, but he continued to sing and perform after the operation. 

Pride was eventually inducted into the Country Music Hall of Fame in 2000. He was also honored with the Willie Nelson Lifetime Achievement Award at the 2020 CMAs. Later that year, Pride passed away due to complications from COVID-19 in December. 

Charley

Artist - Charley Pride

Charley Pride: News, Songs & Reviews | Holler

Charley Crockett has an aura of myth about him. As the distant relative of American folk hero Davy Crockett, he's lived up to his ancestor's name, traveling all over the country and gathering its influences into what he describes as his 'Gulf + Western music', which blends traditional country, honky tonk, blues and soul.  

Playlist

The Best Country Winter Songs

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