By Allen Halas OnMilwaukee Staff Writer Published Jul 13, 2025 at 9:31 AM

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After night one of the featured concerts at Harley-Davidson Homecoming came to an abrupt ending, a sold-out Veterans Park crowd was ready for a party in Milwaukee on Saturday night. Fortunately, one of country music’s most exciting crossover acts was ready to provide the soundtrack.

While the skies were still grey and the threat of rain wasn’t entirely zero, Chris Stapleton took to the Harley-Davidson Stage ready to raise a little hell with thousands of bikers as part of his “All American Road Show” tour. Without much fanfare, he and his band calmly walked onstage to open things up with “Bad As I Used To Be” from “F1: The Movie,” a song that features a steady groove and plenty of clever guitar work from the country crooner, but also set the tone for the rest of the night. 

In fact, Stapleton would tell the Veterans Park crowd that they weren't going to talk much, but rather try to get as much music into their 90-minute time slot as possible, and that's exactly what they did. There wasn't much time to vamp or pander; rather just deliver song after song from a rich catalog of outlaw-tinged country. 

While many artists would tour behind a new record, Stapleton’s most recent album is 2023’s “Higher,” and it’s one that he noticeably stayed away from on Saturday night. Only a few songs from the 14-track album made it to the setlist, with “White Horse” getting the best reception of the tracks that did make the cut. For many artists, that may have been a problem, but with as many must-plays in his early work as Stapleton has, it ended up playing in his favor. 

While playing, Stapleton appeared reserved, with a right-to-work demeanor when it came to each song. That is, of course, while still being able to casually deliver proficient guitarwork whenever he felt like he needed to, and carrying vocals along with his wife, Morgane, by his side. The duo would harmonize with one another with an intimacy about it that felt like you were a guest in their living room, with about 50,000 other houseguests. 

Chris Stapleton performs at Veterans Park as part of the 2025 Harley-Davidson Homecoming Festival in MilwaukeeX

One of the nuances of playing a specialty festival like the Harley-Davidson Homecoming is that, while sold-out, there is still a contingent of people at the festival grounds simply there to celebrate Harley culture, and maybe not so much to see Chris Stapleton. However, you’d be hard-pressed to find a silent crowd member during some of his most recognizable songs, with thousands of supporting vocalists on “Traveller” and “Nobody To Blame” on Saturday. He could also bring things down in a moment’s notice, keeping a special intimacy during ballads like the title track to 2020’s “Starting Over.” He simply knows how to captivate as a performer, and that was once again evident, even with a crowd of bikers that were there to get a little rowdy.

When it was time to call it a night, Stapleton and his band unloaded a string of big songs back-to-back, including “You Should Probably Leave,” a song that hits differently when the husband-and-wife duo are looking at one another while performing it. “Broken Halos” and “Fire Away” followed, to big receptions, and everyone knew that the night would finish with a crowd singalong to breakout hit "Tennessee Whiskey.” The initial set went just north of 80 minutes, with no real stoppages or slowing down Stapleton’s roll. He would sing the names of the band during the breakdown of “Tennessee Whiskey,” hit the chorus one more time, then make his exit.

A one-song encore may have been Stapleton’s classiest move of the night, however. In lieu of getting an actual performance from Hank Williams Jr. on Friday night, Stapleton and the band worked out a rendition of “All My Rowdy Friends Are Coming Over Tonight” for the Milwaukee crowd. It was a special cover, and featured Stapleton belting out the vocals with an added gusto. The cover felt just as fun for the band as it did the Veterans Park crowd, as it was certainly a one-off for the tour. 

Chris Stapleton is a savvy performer, and on Saturday night at Veterans Park, he gave the Harley-Davidson Homecoming concerts a send-off that felt earned after Friday’s weather cancellation. He was most definitely the right call to cap off the weekend of concerts, and one that kept Milwaukee hanging on to his every move.