Country singer Dierks Bentley [ tickets ] is wrapping up the Canadian leg of his Locked & Loaded outing this week, just in time to hit the road with Cross Canadian Ragweed [ tickets ] for round three of his High Times and Hangovers tour.

The nine-city run kicks off Feb. 1 in Chicago and hits Midwestern and Southeastern states, stopping in bars and clubs ranging from 500 to 900 seats.

"My business manager is referring to this tour as the 'how much fun can we have and how much money can we lose tour!'" Bentley joked in a press release. "It's definitely all about the music and good times. Our set will be stacked with mostly old country cover songs and a few of our hits. Staying true to the tour's name, I'm sure we'll be playing old Cash and Waylon songs well into the early morning."

The relentlessly touring Bentley and his band will recover from the Hangover trek with a Feb. 10 performance at NASCAR's annual Budweiser Shootout, which will be broadcast live on the FOX Network from Florida's Daytona International Speedway. Then it's off to Los Angeles for the Grammy Awards, where Bentley is up for Best Male Country Vocal Performance and Best Country Song for his hit single "Every Mile a Memory."

The song is off of Bentley's third studio album, October's "Long Trip Home," which topped Billboard's country album chart and has been certified gold by the Recording Industry Association of America. Several tunes from the album are streaming at Bentley's MySpace page.

The singer/songwriter's first two albums, 2003's "Dierks Bentley [ tickets ]" and 2005's "Modern Day Drifter" have both reached platinum status, according to the RIAA.

March 20 will see the release of Bentley's first ever live concert DVD, "Live and Loud at the Fillmore," which was shot last June at Denver's Fillmore Auditorium in front of a standing-room only crowd, according to a press release. The DVD was directed by London-based filmmaker Russell Thomas. Bonus footage will take fans behind the scenes of Bentley's life of the road.

"Making a live DVD has been a dream of mine for a couple years now," Bentley said in a statement. "I really wanted to capture what we were doing in our live show at that particular moment, and I think Russell did an incredible job putting it on film. This is the ultimate accomplishment for me, the band and our fans."

The Phoenix native toured more than 300 days last year, according to his website. Apparently, the hard work paid off, as 2006 saw the entertainer score multiple award nominations, a No. 1 album, three No. 1 singles and his first headlining tour.