While on the 2025 Outlaw Music Festival circuit, Bob Dylan changed up his usual setlist, playing what is a greatest hits show by his standards.
After seeing the 2025 Rough and Rowdy Ways Tour North America conclusion, which has its own charm, it was surprising to see Dylan break out some of his biggest hits when the Outlaw Music Festival stopped in Columbia, Maryland, on Sunday, Sept. 14, 2025.
Now, context is needed when discussing what a Bob Dylan greatest hits show looks like. Unfortunately for the fan who yelled “play something good!”and begged for “Like a Rolling Stone” in Williamsport earlier in the year, he does not play Highway 61 Revisited's opening song. If it's any consolation, he does play “Highway 61 Revisited.”
Bob Dylan's Outlaw Festival show review
Sandwiched between Sheryl Crowe and Willie Nelson, two greats in their own right, Dylan and his band made their way to the stage hidden behind minimal stage lighting. It was hard to tell when they came out, as the stage was not lit up at all until they began playing. Even then, the stage was only illuminated by a few red stage lights, barely making the band members distinguishable.
Nonetheless, Dylan kicked into his set with a rendition of “Masters of War.” The chilling guitar part is replaced with a bluesy arrangement.
Considering he has opened other shows during the 2025 Outlaw Festival circuit with the likes of “Positively 4th Street” and “Gotta Serve Somebody,” “Masters of War” may seem like an uninspired choice. At least it's from one of his earliest albums.
Being a Bob Dylan fan means you're a glutton for punishment. He has broken out old hits like “Mr. Tambourine Man,” “The Times They Are A-Changin',” “Just Like Tom Thumb's Blues,” “Rainy Day Women #12 & 35,” and “Don't Think Twice, It's All Right,” and only one has made the setlist consistently. What is given can be taken, as they say, and Dylan proves that.
Still, he makes the most of his hour-long slot. His cover of Bo Diddley's “I Can Tell” brings new meaning to the song as the 84-year-old Dylan sings it, and he also covered “Axe and the Wind” and “I'll Make It All Up to You.”
An underrated gem
The first highlight, though, is “To Ramona,” originally from his Another Side of Bob Dylan album. Its waltz — which makes it feel like riding on a merry-go-round — is still retained in the new arrangement, and the harp was a nice addition to the song.
At this point in the song, it became clear that Dylan sounded better than in April. Perhaps that's due to Merriweather Post Pavilion being an outdoor venue rather than an old theater.
Unlike last time, you could understand most of what Dylan was saying. This helps songs like “Under the Red Sky” and “Desolation Row.”
Dylan played that at his 2025 Rough and Rowdy Ways Tour finale in April. However, given its sped-up arrangement, it was nice to be able to clearly make out what he was singing.
Playing the hits
Another standout is the new arrangement of “All Along the Watchtower.” While it isn't as fast as the original, bits of the original guitar riff can be heard. It retains the identity of Dylan's original song while maturing it for an older, wiser Dylan.
Some lesser-known songs like “Love Sick” from Time Out of Mind and “Blind Willie McTell” were then played. They were nice additions to round out his setlist.
The show concludes with back-to-back hits. “Highway 61 Revisited,” even without its signature whistle, maintains its power with its religious imagery.
But nothing beats hearing “Don't Think Twice, It's All Right” from his Freewheelin' Bob Dylan album. His fast guitar picking is replaced by a slower, piano-driven arrangement.
This allows Dylan to slowly make his way through the verses. Through the years, the song has undergone several transformations. In the '70s, he played a reggae rendition, which was unique. The piano ballad drives the song's melancholic lyrics home as an aged Dylan looks back at his life. The song is seemingly about a relationship — “I ain't a-saying you treated me unkind / You could've done better but I don't mind / You just kinda wasted my precious time / But don't think twice, it's all right,” he concludes.
Should you see Dylan on the Outlaw Music Festival?
If you were disappointed by the Rough and Rowdy Ways Tour, seeing Dylan during the Outlaw Festival is a good remedy. Casual fans should recognize 20% of the setlist, and die-hard fans will love every pick.
Rough and Rowdy Ways has its own place in the Dylan canon. It's a very good album, but the arrangements blend together, and it's not a fun listen live.
The Outlaw Festival is Dylan at his best. He actually appears to be having fun with the songs. The setlist is able to be opened up to his whole discography.
His voice is also better than it has been in years, giving fans yet another reason to see him now. He is singing with clarity and conviction. His catalog has continued aging with him, making the performances resonate more than ever.
If there was one disappointment, it would be that he dropped “Positively 4th Street” from the setlist. He sounded amazing singing it earlier in the 2025 Outlaw Festival circuit.
No one can understand the mind of Bob Dylan, though. He is an enigma that is fascinating to observe. His performances feel like you're watching a very tight rehearsal (he didn't acknowledge the Maryland crowd once), and yet, you can't look away.
Bob Dylan's setlist from the Outlaw Festival show in Columbia, Maryland
Below is Dylan's full setlist from the Outlaw Festival show in Columbia, Maryland, on September 14, 2025.
- “Masters of War”
- “I Can Tell” (Bo Diddley cover)
- “Forgetful Heart”
- “Axe and the Wind” (George “Wild Child” Butler cover)
- “To Ramona”
- “Early Roman Kings”
- “Under the Red Sky”
- “I'll Make It All Up to You” (Jerry Lee Lewis cover)
- “‘Til I Fell in Love with You”
- “Desolation Row”
- “Love Sick”
- “Share Your Love with Me”
- “Blind Willie McTell”
- “Soon After Midnight”
- “Highway 61 Revisited”
- “Don't Think Twice, It's All Right”
