Bringing out some heavy hitters. There’s no doubt that Dierks Bentley has been one of the most important and ultimately intriguing artists in the mainstream. From his longtime relationship with Cross Canadian Ragweed’s Cody Canada to his unabashed love for bluegrass, namely working with the likes of Billy Strings and recently The Band Loula, the “Sideways” singer has always been an interesting figure in the genre. Of course, that’s not even mentioning the fact that he selected the first-ever Traditional Country Album of the Year Grammy winner, Zach Top, to open for him on his most recent Broken Branches tour. Simply put, despite being a mainstream mainstay for the two decades at this point, Bentley has long been a torch-bearer and champion for some of the best young and otherwise underrated talented flying out of both the bluegrass and alt. country scene. As we head into 2026, it looks like nothing is changing. Just announced this morning, Bentley will be hitting the road this summer with an absolutely stacked set of openers, including the likes of bluegrass legend, Ricky Skaggs, Kaitlin Butts, Mountain Grass Unit, Cole Goodwin and Owen Reigling on the Off The Map Tour. In total, the Off The Map Tour will hit 11 cities on a six-week run in June and July. Beginning in Rogers, Arkansas, on June 12th, Bentley and Co. will hit amphitheaters in Kansas City, Colorado Springs, Charleston and more before wrapping up on July 18th in St. Augustine, Florida. Discussing the tour, which is named after a track on his last album, Broken Branches, the “I Hold On” singer would express how excited he is to hit the road with Skaggs “‘Off The Map’ is a song about going to that place where you take a break from it for a little bit, whether it’s a bar stool sipping something cold, or a back porch down a back road. I like to think that our shows are a place where our fans can go off the map for a few hours, and recharge the batteries. The band and I are so excited about sharing the road with the one and only Ricky Skaggs, as well as with the other guys and girls on the shows with us this summer. They were all hand picked, as I am big fans of theirs. Can’t wait to get out there and watch their shows before we get to go out and do our thing. Going to be some great on-stage collaborations this summer.” Members of Bentley’s fan club, The Risers, will have first access to presale opportunities starting on Tuesday, February 17th. General sale for the Off The Map Tour will officially open to the public on Friday, February 20th at 10 a.m. local time. In addition to announcing the tour, Bentley and Skaggs would also team up for an absolutely killer rendition of his 2007 #1 hit, “Free and Easy (Down the Road I Go).” Leaning heavily into all the bluegrass elements present on the original, Skaggs masterful mandolin picking here simply sounds lovely in addition to the banjo, upright bass and more featured in the new video. Watch here: View this post on Instagram Off the Map Tour Dates 6/12 – Rogers, AR < ~ 6/13 – Kansas City, MO < ~ 6/25 – Bonner, MT ! # 6/26 – Airway Heights, WA * # 7/2 – Colorado Springs, CO < # 7/9 – Gilford, NH < * 7/10 – Bridgeport, CT < * 7/11 – Canandaigua, NY < * 7/16 – Wilmington, NC < # 7/17 – Charleston, SC < # 7/18 – St. Augustine, FL < # < Ricky Skaggs & Kentucky Thunder * Kaitlin Butts # Cole Goodwin ~ Owen Riegling ! Mountain Grass UnitThe post Dierks Bentley Announces New Tour, Teams Up With Ricky Skaggs For Killer Performance Of “Free And Easy (Down The Road I Go)” first appeared on Whiskey Riff.