Dierks Bentley rode into Nashville Sunday afternoon (Oct. 17) with a gang of his big-hearted motorcycle buddies for his fifth annual Music & Miles for Kids benefit event. The day started early with a group motorcycle ride that began in Columbia, Tenn., and culminated in downtown Nashville with a concert that also featured Luke Bryan, Laura Bell Bundy, Mat Kearney, Miranda Lambert, Del McCoury, Heidi Newfield and Jerrod Niemann.

Prior to Sunday's event, Bentley had already raised $1.2 million through his Miles & Music for Kids fundraisers. The latest ride and concert added another $250,990 to the total including $10,000 from a guitar auctioned onstage. The Nashville fundraiser benefited the Monroe Carell Jr. Children's Hospital at Vanderbilt, a Children's Miracle Network Hospital.

Bentley became interested in the cause after a close friend's child needed treatment at the Vanderbilt facility. At the time, the singer did not have kids of his own. Now with a daughter, Evie, and another child on the way, the charity has taken on an even more personal meaning. In five years, the Miles & Music program has grown from a small, hometown party into a nationwide effort that this year spread to Atlanta, Dallas, Phoenix and Seattle.

With a warm fall day at Nashville's Riverfront Park, hundreds of motorcycles were parked along First and Second avenues. At the concert, fans were treated to more than three hours of music with an off-the-cuff feeling, held together by the antics of host Laura Bell Bundy. She kept the crowd -- and the musicians -- on their toes by taking on two alternate personalities complete with costume changes. The former Broadway actress also opened the show with a short set that included "Giddy On Up."

With his up-tempo, wind-in-your-hair style tunes, Bentley's music goes over extremely well with the biker crowd. About half of the audience was wearing Harley-Davidson apparel, and they cheered and toasted as the singer dedicated "Lot of Leavin' Left to Do" to them and their freewheeling ways. His set list was tailor-made for the riders and loosely followed a theme that spoke to motors, screeching tires and open spaces. "Feel That Fire," "Sideways" and "Up on the Ridge" kept the crowd swaying in groups or cuddled up close on blankets as the sun crept down beneath Nashville's skyline.

But as he took the stage periodically to sit in on the other performers' songs, Bentley's collaborations were highlights of the show, even as he jokingly warned that the musicians were "trying to trip ourselves up" by playing together without rehearsing. His modesty was quickly brushed aside, though, as each one seemed to fit together better than the last.

Even when he and Luke Bryan playfully fumbled the ending of a medley of the Nitty Gritty Dirt Band's "Fishin' in the Dark" and Collective Soul's "Shine," the audience seemed only to love the handsome pairing of singers more. It was obvious from the start that the concert was more of an exercise in friendship and camaraderie, anyway, and the crowd was more than happy to feel a little closer to the artists. Bentley himself acted like each audience member was a long-lost friend, relating personal stories from the road and talking a little shop with the riders. Bryan's five-song set also included his current single, "Someone Else Callin' You Baby."

Earlier in the concert, Bentley performed three songs with the always-quick-with-a-comeback Miranda Lambert, who teased him by saying that "White Liar," "Gunpowder & Lead" and the bluesy, soulful rendition of "Bad Angel" were about him. Bentley, Lambert and Jamey Johnson are nominated for a CMA vocal event of the year award for the latter track, and even with Johnson's part being handled by Jerrod Niemann, the song's gritty harmony and rolling pulse stayed intact as a bluegrass-inspired standout. Lambert also performed "Kerosene" and a quiet rendition of "The House That Built Me," backed only by an acoustic guitar.

One of the reasons "Bad Angel" came off sounding so inspired by bluegrass might have been the fact that Del McCoury was on hand for Sunday's concert. The track is featured on Bentley's acoustic album, Up on the Ridge, and the Travelin' McCourys -- a band featuring McCoury's sons -- toured with Bentley in support of the record. Widely recognized as favorites in the bluegrass world, Bentley clearly looks up to the seasoned performers.

"Those guys are a big reason I stuck around [Nashville]," he remarked quite matter-of-factly.

The singers -- using Bentley's raspy baritone and McCoury's soaring tenor to full effect -- traded verses on "Roll On, Buddy, Roll On," a song McCoury remembered playing with Bill Monroe for the first time in 1963.

Nashville-based singer-songwriter Mat Kearney ("Closer to Love," "Nothing Left to Lose") whipped the crowd up when Bentley put him on the spot, asking him to choose a song to cover. Tom Petty's "Learning to Fly" was the pick, and yet another interesting harmony was struck.

During the concert, the crowd provided warm welcomes to Niemann and Heidi Newfield for hits such as his "Lover, Lover" and Newfield's ode to idyllic romance, "Johnny and June."

"Free and Easy (Down the Road I Go)" closed the night for Bentley, but not before he could tell us where that road was leading. Miles & Music for Kids events will be held next year in Nashville, Chicago and Columbus, Ohio.