The Outlaw Music Festival is one of the biggest draws of the summer here in Bangor, and we want to send a lucky listener to this nearly sold-out show.

It's no wonder this show is so popular. Music icons Willie Nelson and Bob Dylan, joined by Sheryl Crow, will perform at the Maine Savings Amphitheater on Friday, Sept. 5, 2025.

We're fortunate to be able to send some of our listeners to the great shows down on the waterfront. With these legends on the stage, this will be one of the best of the summer.

Getty/TSM
Getty/TSM
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Willie Nelson and Family are incredible on stage. Nelson is a country music icon whose career has spanned decades, featuring such classic songs as "Always on My Mind," "On the Road Again," "Pancho and Lefty," and "Blue Eyes Crying in the Rain."

Frankly, there are too many classic songs to name. The same goes for Bob Dylan, a master poet and bona fide musical genius who won the Nobel Prize for literature in 2016.

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Dylan's catalog is among the most impressive and diverse in the history of music. His works include the folk anthems "The Times They are 'a Changin'", "Blowin' in the Wind", and "Masters of War" (which we hear he performs on this tour). If that weren't impressive enough, he's also responsible for such songs as "Like a Rolling Stone," "Subterranean Homesick Blues," and "Tangled Up in Blue."

Sheryl Crow is a modern music force in her own right, with songs including "All I Wanna Do," "Soak Up the Sun," and "If It Makes You Happy."

Okay. Without further ado, here's what to do to enter to win tickets to this incredible show.

Enter your information below. We'll contact our winners on Wednesday, Sept. 3, to give you time to make your plans to come to Bangor and join the crowd.

Of course, not everyone can win. Here's where to buy tickets.

Good luck, loyal listeners. Hopefully, we'll see you at the show.

30 Pictures of a Young Willie Nelson

Willie Nelson began his music career in the late 1960s. Back then he wasn't the typical country artist from Nashville — he was considered an outlaw.

Take a look back to his early years, and see photos of a young Willie Nelson that you may have ever seen before.

Gallery Credit: Evan Paul

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