Country Hitmaker John Michael Montgomery Closes Out Touring Career With Emotional, Sold-Out Farewell in Kentucky
The memorable evening included a surprise moment that left John Michael Montgomery nearly speechless.
John Michael Montgomery; Photo by Logan Couch
The curtain officially came down on John Michael Montgomery’s touring career Friday night with a sold-out, family-filled farewell concert in his home state of Kentucky. The emotional evening featured a lineup of special guests closely tied to Montgomery’s life and legacy, including son-in-law Travis Denning, who opened the show, followed by Walker Montgomery, John Michael’s son, and Montgomery Gentry, featuring his brother Eddie Montgomery.
Held at the iconic Rupp Arena in Lexington, the hometown celebration was packed with unforgettable moments and served as a fitting, heartfelt conclusion to John Michael Montgomery’s more than 30-year run on the road.
The country hitmaker kicked off the night with “Cowboy Love” and went on to deliver hit after hit from his legendary catalog, spanning from his very first No. 1 single, “I Love the Way You Love Me,” to the beloved “I Swear,” which prompted couples throughout the arena to slow dance near their seats. He also paid a touching tribute to the armed forces with “Letters From Home.”
Midway through the show, Montgomery sweetly dedicated “Home To You” to his wife, Crystal, telling her from the stage, “THank you honey for putting up with me for 30 years.”
The country music icon kept the evening mostly down to business, pausing briefly between songs to express his gratitude to fans and introduce the next hit. However, one of the most emotional moments of the night came when his son, Walker, who had performed earlier, returned to the stage.
“Hey Dad, you never left Kentucky… you never moved to Nashville… Kentucky has been your home for all of your life… so we are going to have a special surprise for you,” Walker shared.
Within moments, other family members joined him onstage as Rupp Arena General Manager Brian Sipe unveiled a permanent banner that will hang in the arena, commemorating John Michael Montgomery’s iconic career and The Road Home Tour: The Final Concert on 12/12/25 at Rupp.
“Well I certainly didn’t expect that tonight! As much as I have come here to watch the Cats play, and just absolutely loved seeing those banners, all of those decades and years of greatness hanging from the ceiling of this place, I don’t even have words… I cannot believe it, but I’ll tell you what… That’s the most special thing that’s happened to me in my career,” Montgomery shared, wiping away tears.
As fans sang along to hit after hit, the night served as a powerful reminder of John Michael Montgomery’s lasting impact on country music. Even at 60, his vocals sounded just as strong as ever – that man can still sing!
The show came to a close on a high note with the high-energy “Be My Baby Tonight,” followed by the iconic “Sold (The Grundy County Auction Incident).”
John Michael Montgomery The Final Concert Set List
Cowboy Love
Life’s a Dance
Beer and Bones
No Man’s Land
If You’ve Got Love
How Was I To Know
Long As I Live
Home To You
The Little Girl
Letters from Home
I Love the Way You Love Me
I Can Love You Like That
Rope the Moon
I Swear
Be My Baby Tonight
Sold (The Grundy County Auction Incident)
Ahead of the show, we caught up with John Michael Montgomery to talk about the history-making night. The country icon admitted the moment arrived faster than he ever expected.
“It’s hard to believe it’s time. A couple years ago when I told everybody I was ready to get off the road from tour, it seemed like it was like two years away and it just went by too fast,” he admitted to Country Now. “But being able to do it right here, I didn’t realize at that time that my last show would be here in my favorite venue, first of all. So being able to finish up my touring career right here, where I’ve watched the Wildcats play, I’ve watched all kinds of great concerts and be able to get on stage and perform all my hits from the late 1900’s for all these folks. It is going to be a special night for me.”
Montgomery went on to admit he knew the evening would be an emotional one.
“I mean, it’s just kind of hard to believe it’s been 33 years since I was playing a nightclub right down the road from here for $5 a door charge to playing here and thinking it’s gone by that fast and where’d it go? All that stuff goes through your head. And of course, just turning 60 this year and everything, having a new grand baby and all that stuff, I’m getting off the road, but I ain’t slowing down any!”
Throughout his career, John Michael Montgomery amassed 36 hit singles, including seven No. 1 songs, and released 11 studio albums that have earned multi-platinum and gold RIAA certifications, solidifying his place as one of country music’s most enduring voices.
Lauren Jo Black is a longtime country music journalist, editor, host, and media personality whose work has helped shape the conversation around country music for nearly two decades. As the current Editor-in-Chief of Country Now, she has become one of the genre’s most respected voices, interviewing hundreds of country music’s biggest stars, including Dolly Parton, Garth Brooks, Reba McEntire, Shania Twain, Randy Travis, Luke Bryan, Carrie Underwood, Blake Shelton, Luke Combs, and countless others. Over the course of her career, Black’s written work and interviews have reached billions of country music fans worldwide. A 2009 graduate of the University of Central Florida, Black began her career by founding Country Music Is Love, one of country music’s earliest independent digital publications, which she later sold to a major record label in 2015 before it was rebranded as Sounds Like Nashville. She then served as the publication’s Editor-in-Chief for more than two years. Her work has also appeared in Forbes, and she previously served as the Country Music Expert for Answers.com. Widely recognized for her expertise, Black has appeared as a featured guest on The Bobby Bones Show, BobbyCast, and Scripps News Morning Rush, providing insight on country music’s biggest moments. She has also hosted Country Now Live, a concert series featuring performances from artists including Lady A, Dierks Bentley, Riley Green, Jordan Davis, Dustin Lynch, Gabby Barrett, Brett Young, Jon Pardi, Kip Moore, Chris Young, and more. The series has welcomed thousands of fans in person while reaching millions more online. In addition, she hosted Connect With Country Now, a weekly interview series featuring conversations with rising country stars. Throughout her career, Black has earned a reputation for discovering and championing artists long before they become household names. She has covered Luke Bryan since the early days of his career, beginning when he was writing songs for other artists, including Billy Currington’s No. 1 hit “Good Directions,” before stepping into the spotlight with his debut single, “All My Friends Say” and eventually becoming one of biggest names in music. She also gave Megan Moroney her first opportunity to walk a major red carpet as Country Now’s official guest correspondent at the 2022 CMA Awards. An interview she conducted in 2018 for Forbes.com with Luke Combs that inspired his multi-week No. 1 hit, “Doin’ This.” She has also hosted stages at CMA Fest, moderated an industry panel at Country Radio Seminar, and helped lead important conversations about the evolving landscape of country music media. Beyond journalism, Black has also used her platform to support charitable causes and highlight organizations making an impact. Through Country Now Live, she has helped raise awareness and support for St. Jude Children’s Research Hospital, while also advocating for animal rescue through Country Now’s Pupdate series, spotlighting organizations including MuttNation Foundation, Wags & Walks, and Proverbs 12:10 Animal Rescue. Black has been recognized as one of Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. She is a longtime member of both the Country Music Association (CMA) and the Academy of Country Music (ACM). After nearly 20 years covering country music, Lauren Jo Black has spent her career telling the stories behind the artists, songs, and moments that have shaped the genre. Her first-ever book, Country Music Forever: An A-to-Z Celebration of Icons, Songs and Stories, brings that same passion and firsthand knowledge to the page, celebrating not only the legendary artists and timeless songs that have become the soundtrack to generations of fans, but also the places, traditions, and cultural moments that have made country music one of the most beloved genres around the world.
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