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John Michael Montgomery Caps Off 30-Year Touring Career With Triumphant Rupp Arena Show

December 18, 2025/by Lorie Hollabaugh

John Michael Montgomery

John Michael Montgomery said goodbye to the road life and wrapped his 30-plus year touring career in front of a sold-out crowd in a special farewell show at Lexington, Kentucky’s Rupp Arena on Friday night (Dec. 12.)

The heartfelt evening was a full-blown family affair as well, with John Michael’s son-in-law Travis Denning opening the night of performances, followed by John Michael’s son Walker Montgomery, and Montgomery Gentry, featuring Eddie Montgomery, John Michael’s brother.

Loyal fans, family and friends gathered in Lexington for the superstar’s sendoff, and as Montgomery took the stage and began performing hit after hit, he was interrupted mid-show by Walker, who stepped onstage behind his father and said, “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.”

The rest of the family then joined Walker onstage along with Rupp Arena’s General Manager Brian Sipe, who made an incredible presentation to the country icon by unveiling a permanent banner that will hang in the arena commemorating John Michael’s iconic career and The Road Home Tour, The Final Concert 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!” exclaimed Montgomery, who was genuinely surprised.

The consummate professional continued the show performing many more of his epic hits before ending the night with a rousing encore of “SOLD,” which he invited everyone back onstage to perform with him.

“Congratulations to John Michael Montgomery on a legendary career,” said Outback Presents CEO Mike Smardak. “Working with him and his team on such an unforgettable event was truly an honor.”

“What an unforgettable night celebrating Kentucky’s own John Michael Montgomery,” added Sipe of Rupp Arena. “We were honored that he chose our venue for his final concert, and it was a true privilege for our entire team to raise his name into the rafters at Rupp Arena, cementing his legacy forever,”

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Lorie Hollabaugh
Lorie Hollabaugh
Hollabaugh, a staff writer at MusicRow magazine, has over 20 years of music business experience and has written for publications including American Profile, CMA Close Up, Nashville Arts And Entertainment, The Boot and Country Weekly. She has a Broadcast Journalism and Speech Communication degree from Texas Christian University, (go Horned Frogs), and welcomes your feedback or story ideas at lhollabaugh@musicrow.com.
Lorie Hollabaugh
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https://musicrow.com/wp-content/uploads/2025/12/John-Michael-Montgomery.jpg 812 1220 Lorie Hollabaugh https://musicrow.com/wp-content/uploads/2019/03/MusicRow-header-logo-Mar19B.png Lorie Hollabaugh2025-12-18 15:22:282025-12-18 15:22:28John Michael Montgomery Caps Off 30-Year Touring Career With Triumphant Rupp Arena Show

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