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    Home » News » Dierks Bentley Joins Cross Canadian Ragweed For Performance Of “42 Miles” During Night One Of The Boys From Oklahoma Concert

    Dierks Bentley Joins Cross Canadian Ragweed For Performance Of “42 Miles” During Night One Of The Boys From Oklahoma Concert

    Brennen KellyBy Brennen KellyApril 11, 2025 News
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    Cross Canadian Ragweed, Dierks Bentley
    Photo Credit: @willhuckabee (TT)
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    Ragweed is officially back.

    For many in the red dirt scene, last night in Stillwater, Oklahoma, was nothing short of a milestone. After a 15-year hiatus, Cross Canadian Ragweed took the stage for just the second time since 2010 for the first of four shows in their weekend-long Boys From Oklahoma concert series.

    Joined by the likes of fellow red dirt legends, the Turnpike Troubadours, The Great Divide, Jason Boland & The Stragglers and Stoney LaRue, Ragweed made their triumphant return to a sold-out crowd of over 45,000 people at Boone Pickens Stadium.

    After Turnpike, The Great Divide, Boland and LaRue warmed up the crowd, it was Ragweed’s time to step onto the stage and give the fans what they’d been craving for a decade and a half. Midway through the 26-song set after performing setlist staples such as “17,” “Sick and Tired” and “Constantly,” the Oklahoman band brought out none other than longtime friend and mainstream staple, Dierks Bentley, to perform his personal favorite song, their severely underrated 2001 track, “42 Miles.”

    For those unaware of the Bentley and Ragweed connection, the “What Was I Thinkin'” singer and band have a long history. Most notably, Bentley references them in his 2006 smash hit, “Free and Easy (Down the Road I Go),” where he sings, “Ragweed rockin’ on the radio.”

    The connection goes even deeper, however. Ragweed actually opened up for Bentley all the way back in 2006 during his first headlining tour, High Times and Hangovers. During their time together, the 49-year-old singer/songwriter formed an incredibly close relationship with Ragweed’s front man, Cody Canada. The relationship was so impactful to Canada that he named his first son after the “Settle For A Slowdown” singer.

    On a night full of high emotions from fans and the band alike, Ragweed as well as Bentley, did not disappoint and delivered a knockout performance. It’s hard to pick one standout moment from a night like this; however, with all the history between the two artists, this just might be it.

    Watch here:

    @willhuckabee

    The greatest night of my life! #dierksbentley #crosscanadianragweed #boysfromoklahoma #oklahoma #stillwater #fyp

    ♬ original sound – Will Huckabee

    @brittenmw

    Of all the guest appearances that one was the most surprising #boysfromoklahoma #reddirtmusic #stillwater #livemusic

    ♬ original sound – Britten Wallace

    Cross Canadian Ragweed Dierks Bentley
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    Treaty Oak Revival’s Sam Canty Crowd Surfs During Cup-Flying Performance Of “Boomtown” At Syracuse Show [Watch]

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    September 25, 2026

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