Dierks Bentley heads to the New York City on Monday, October 18, to kick off a series of four consecutive shows, beginning with his regular country concert at New York City's Bowery Ballroom. He follows that with three more shows at three different locations -- on Tuesday, October 19, he'll set up for a show at the City Winery, followed the next night by a very intimate songwriters' showcase at Joe's Pub. The last night (Thursday, October 21), he'll thrill audiences with a show at Southpaw in Brooklyn.

All four shows are going to be quite different from each other, which is both thrilling and terrifying for singer. "It's a lot of work, in a good way. It's a lot of wood-shedding," Dierks tells The Boot. "The first night is going to be my country band, which will be a total blast, and we'll do songs off the 'Up on the Ridge' record, plus all the hits. The second night is with the Del McCoury Band, and I assume with those guys I'm probably going to do songs off the 'Ridge' record and also some songs of Del's that I really like and some traditional bluegrass songs and just kind of pick on their catalog."

"The third night will be just sitting in a chair with some of my best friends -- Jon Randall, his wife Jessi Alexander who wrote 'The Climb,' and is one of the greatest singers in town. And then Jim Beavers, who I've written a lot of songs with, who's one of the funniest human beings I've ever met in my entire life. That's always a cool thing, because that Joe's Pub really has a steady following of people who love country music and love hearing the songwriters."

"The fourth night is with the Punch Brothers, and those guys cut three tracks on my record," Dierks says. "I'm still trying to figure out what I want to do with those guys because they can play Mozart and Bach and Radiohead, and they're so talented, so I want to cover some really cool covers and do some stuff off my record. I really need to figure out a way to fit in musically with them, because they're such a tight, five-piece band ... I'm glad it's the last night, because it'll be the most technically-challenging shows. It'll be a good test, and this whole year has been kind of about testing myself."

Dierks doesn't figure he will get in much sightseeing while in New York, but during his previous trip to help announce this year's CMA awards nominations, he was able to take his wife, Cass, on a date night. "We went and saw 'Rock of Ages,' which was just unbelievable. It just gives you such respect for how talented those people are, and the show is hilarious."

Dierks, who is up for three CMA awards including Male Vocalist of the Year, is headed across the border following his New York shows. He's scheduled to perform in East Windsor, Ontario, Canada on Friday, October 22. But first, he will be in Nashville on Sunday, October 17, for his fifth annual Miles & Music for Kids celebrity motorcycle ride and concert. For his full tour schedule, check here.

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