A Holiday Song With Heart
North Carolina-grown and Nashville-based Trey Calloway has built a career grounded in authenticity, soulful storytelling, and a deep connection to his roots. Long before collecting millions of streams and winning Songwriter of the Year at the Texas Country Music Awards, he was a church-raised gospel singer who fell in love with the grit and emotion of ’90s country. He has since opened for acts like Joe Diffie, Tracy Lawrence, McBride & The Ride, Pat Green, and Craig Campbell, and has performed on notable stages including Billy Bob’s Texas, the House of Blues, and the Charlotte Speed Street NASCAR Festival.
Calloway joined Country Evolution for an interview and exclusive premiere of the live performance video for “Christmas With You,” a song he originally released last year and felt compelled to revisit. For years, fans had urged him to record a Christmas track, but he wanted his first holiday release to have substance. “I wanted to do something not like ‘Jingle Bells.’ I wanted to do something with some meat to it,” he said.
The inspiration came from his own life. For the past four years, Calloway has lived in Nashville while his wife remained in South Carolina. He also shares a son from a previous marriage who lives in Charlotte. “I’ve really struggled with being away from the love of my life and being away from my son,” he explained. “This is a tough life… being gone all the time.” The song grew from those emotions and expanded into a tribute to everyone who spends the holidays apart from those they love, from musicians to truck drivers and military families. “You never really hear anybody talk about that reality,” he added. “So, yeah, that’s the inspiration behind the song, missing my family and wishing I was with them.
Filming the Video
The newly premiered live version was intentionally raw. Calloway teamed up with producer Jesse Savio and filmed the performance in a small, atmospheric studio featuring a striking stained-glass window. With just two or three takes, minimal post-production, and his friend Dom Sotis behind the camera, the goal was to capture honesty. “We basically just let the microphones record and I played the song,” Calloway said. “I kind of like the rawness of what we did.”
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Making the Most of Time at Home
Because of his demanding schedule, quality time with his family is carefully protected. “My calendar is so crazy organized,” he said with a laugh. When he gets back to South Carolina, he and his wife make a point to slow down and visit Brookgreen Gardens, a beloved holiday tradition known for its Night of a Thousand Candles display. “It always puts me in the Christmas spirit.”
They also visit her family in Ohio each December, where they bake Christmas cookies with her grandmother, a tradition that has become especially meaningful following the recent passing of his own grandmothers. “Those times don’t last forever, and while you have them, you have to take advantage of them,” he said.
Favorite Traditions and Childhood Memories
Calloway is firmly on Team “Christmas Starts After Thanksgiving.” Once dessert is finished, he’s ready for decorations, lights, and the full holiday experience. His dad, he joked, transforms his yard into something straight out of the Griswold house, while his wife decorates a massive family heirloom tree loaded with decades of ornaments.
His most treasured childhood Christmas memories come from holiday gatherings at the Lake Norman home of his great-grandparents, Joe and Edna Wentz. “There would be like sixty of us in this old house from the sixties,” he recalled. “So I have the fondest memories of being over there.” Calloway expressed how beautiful it was, spending time with his extended family and savoring the moment.
Looking Ahead: New Album, Touring, and a Big Year in 2026
As 2025 wraps, Calloway is proud of the momentum he’s built. “We’ve just put out song after song after song, and people are really starting to pay attention,” he said. His streaming numbers continue to grow, and fans increasingly show up at concerts wanting to hear his originals.
On a personal level, he is most proud of balancing his career with being present for his son. “It is not a sacrifice. It is an honor to be his father,” he emphasized.
Looking to the new year, Calloway is already deep into recording his next album with producer Phil O’Donnell. “I’m super excited about this record,” he said, describing O’Donnell as a mentor who has taken him under his wing. A new booking deal also means 2026 will bring his first true tour as a solo artist. “I’m really excited to hit the road.”
Fans can expect the first single in late spring or early summer, with tour dates rolling out around the same time.
For now, he’s soaking in the holiday season and celebrating the heartfelt story behind “Christmas With You,” brought to life in a simple, honest live performance.
