Awards
2025 INSPIRATIONAL COUNTRY MUSIC ASSOCIATION SOUND OF SMALL TOWN AMERICA FINALIST
As a 2025 regional winner of The Sound of Small Town America, Trey Calloway has qualified to play as an Inspirational Country Music Association finalist at The Grand Ole Opry in 2026!
2024 TEXAS COUNTRY MUSIC ASSOCIATION RUNNER-UP, CHRISTIAN SONGWRITER OF THE YEAR & 2023 TCMA WINNER, COUNTRY SONGWRITER OF THE YEAR
Trey Calloway received 2024 runner-up honors as the Texas Country Music Association (TCMA) Christian Songwriter of the Year for both of his original songs “Horses In Heaven” and “Backroad Believer”. Trey also won the 2023 TCMA Country Songwriter of the Year Award for his original song “One Tough Job,” and an Honorable Mention Award for his song “You Are.” Trey performed his award-winning song at the TCMA Awards held in November 2023 at Billy Bob’s Texas Stockyards in Fort Worth!
2025 JOSIE NOMINEE & 2024 JOSIE MUSIC AWARDS WINNER
Trey Calloway is currently nominated for 5 Josie Music Awards in 2025 for Artist of the Year, Vocalist of the Year, Social Impact & Holiday Songs of the Year and Songwriter Achievement. In 2025, nearly 86,000 JMA submissions were received, with 2.8% receiving nominations. Trey won the 2024 JMA Vocal Event of the Year for “Workin’ Thang” and had 11 nominations in a field of 75,000 submissions, including for Modern Country Artist, Country and Rock Songs, Vocalist, Songwriter, and Music Video of the Year.
2023 JOSIE MUSIC AWARDS WINNER
Trey won the 2023 Josie Music Award for Modern Country Song of the Year for “Worth A Shot” and was honored to accept his JMA on the Grand Ole Opry stage in Nashville! Trey was nominated for 8 JMAs in 2023 including Modern Country Artist and Male Vocalist of the Year, Best Performance in a Music Video, Best Music Video for “Redneck’s Guide,” and Songwriter Achievement. The JMAs are the largest independent music awards worldwide, receiving almost 60,000 submissions in 2023 with 2.5% receiving nominations.
2022 JOSIE MUSIC AWARDS WINNER
Trey Calloway won the 2022 Josie Music Awards Vocal Competition in Nashville based on live a capella performances of his original songs. Trey also won a 2022 Songwriter Achievement Award for his original music! He was nominated for JMA Country Artist of the Year and Country Male Vocalist of the Year, and his original song “I Don’t Wanna Love You Anymore” was nominated as the JMA Country Single of the Year. The JMAs are the largest independent music awards worldwide, receiving 52,442 submissions in 2022 with 1.8% receiving nominations. The 2022 JMAs were held at the Grand Ole Opry House in Nashville.
2021 JOSIE MUSIC AWARD WINNER
“Heal This Family” won the Josie Music Award’s Social Impact Video of the Year! Trey Calloway was nominated for JMA Entertainer of the Year; Classic Country Artist of the Year; Country Vocalist of the Year; and Social Impact Song of the Year. The JMAs are the largest independent music awards worldwide, receiving 38,000 submissions in 2021 with 2.6% receiving nominations.
INTERNATIONAL SINGER-SONGWRITER ASSOCIATION 2025, 2024, 2023 & 2022 AWARDS FINALIST
Trey Calloway was named as a 2025 finalist by the International Singer-Songwriter Association (ISSA) for Vocalist of the Year and for Album of the Year for “Wanted Man.” He was also a 2024 finalist for Entertainer, Vocalist, Songwriter, Single, Emerging Artist and Music Video of the Year and a 2023 finalist for Music Video of the Year for “Worth A Shot.” In 2022, Trey was a finalist for Rising Star and Songwriter of the Year awards, and his original song “Karaoke Cowboy” was a finalist for Single of the Year.
CAROLINA COUNTRY MUSIC AWARDS SONG OF THE YEAR WINNER & 2023 ENTERTAINER OF THE YEAR FINALIST
Trey Calloway’s song “Tire Tracks” won the Carolina Country Music Awards (CCMA) April 2022 Artist Showdown and “Home Is Where The Heart Is” won the CCMA 2018 Song of the Year and Gospel Song of the Year! Trey was named as a finalist for 2023 CCMA Entertainer of the Year and was previously nominated as the CCMA Male Artist of the Year. The CCMAs are presented annually by The Carolina Country Music Association to recognize musicians who grew up in or reside in the Carolinas.
QUEEN CITY AWARDS NOMINEE 2024, 2023, 2022 & 2021
OTHER HONORS
- 2025, 2024, 2023, & 2022 Nashville Songwriter Association International Designation (NSAI) as “One to Watch”
- 2025 Indie Music Icon Radio Awards Winner for Album of the Year "Wanted Man"
- 2025 Tennessee Songwriters Week Regional Winner & Finalist
- 2025 & 2024 International Fair Play Country Music Awards Nominee, Modern Country & Country Rock Artist, Country & Wedding Songs & Music Video of the Year
- 2025 Finalist & 2024 Semi-Finalist, American Songwriter, Wide Open Country Song Contest
- 2023 World Songwriting Award Winner, Outlaw Song & Music Video for Worth A Shot & 2022 Finalist
- WSOC-FM 103.7 Charlotte Speed Street NASCAR Artist