Road-trippin’ with The Poets and Pirates, a weekend in Pittsburgh!
If there's one thing we've learned since launching The Poets and Pirates back in 2008, it's that every road trip has a story. And our latest trip to Pittsburgh, PA was no exception. Packed gear, full tank, and Kenny Chesney queued up on the playlist — we hit the road for another weekend of beach-country vibes, whiskey laughs, and a whole lotta music.
🚐 On the Road Again
Rolling into Pittsburgh on Friday afternoon, we were greeted with that signature Steel City energy: blue skies, bridges everywhere, and a summer buzz in the air. Shane (our barefoot frontman and Kenny-in-spirit) kept morale high, belting out Chesney classics from the passenger seat — whether the rest of us asked for it or not.
Mason, our guitar slinger, spent most of the drive talking about tones on his amp rig. (He swears tone is in the fingers… and also the pedals… and also the weather.)
Gregg, holding down the bass and low-end dad jokes, kept everyone laughing while giving the occasional geography lesson. (Did you know Pittsburgh has more bridges than Venice? Gregg does.)
Meanwhile, Mike on drums was scrolling Yelp for wings. Priorities.
🎤 Saturday Night: Cadillac Jack's Showdown
Cadillac Jack's is one of those venues where you know it's going to be a party the second you step inside — and boy, was it ever. By the time we hit the stage, the place was packed wall to wall with a wild, ready-to-sing-along crowd.
We kicked things off with "Beer in Mexico", and from the first note, the crowd was all in — singing every word, raising drinks, dancing in flip-flops. It felt like we transported the whole bar to the beach.
Somewhere between "When the Sun Goes Down" and "American Kids", people were jumping, clapping, and high-fiving strangers. We even spotted a couple wearing matching "No Shoes Nation" shirts and pirate hats. Legends.
Shane had them in the palm of his hand, with Mason ripping solos like it was a stadium, Gregg grooving hard like the bass owed him money, and Mike throwing down like he had a personal vendetta against the snare drum. 🔥
🍻 Post-Show Shenanigans: Hotel Bar Tales
After loading out, we headed back to the hotel bar for a nightcap (okay, several). These are the moments people don't always see — where the music winds down, and the stories ramp up.
Shane told us about the time he once accidentally opened for a Journey tribute (long story, wrong venue), and Mason got philosophical about the difference between "party country" and "island country." (There's a chart. He's working on a TED Talk.)
Gregg shared tales from the early days of the band — sleeping in vans, breaking strings mid-show, and once being offered payment in shrimp. (We didn't take it. Probably should've.)
Mike ran point on toasts and drumstick stories — including one about the time a fan caught a flying stick in mid-air and immediately asked if it was autographed. (It wasn't. It is now.)
🏁 Back on the Road, Already Missin' It
The ride home on Sunday was quieter — a little road-weary, a little hungover, but still buzzing from the night before. Pittsburgh showed us big love, and Cadillac Jack's delivered a night we won't forget. New fans, new friends, and new stories to add to the book.
🎟️ Want to Be Part of the Next Chapter?
Whether you're a venue looking to book the original Kenny Chesney tribute band, or just a diehard No Shoes fan wanting the full live experience — The Poets and Pirates bring the party every single time.
Available nationwide
Weddings, festivals, private parties, corporate events
Booking info at kennychesneytribute.com
We don't just play Chesney's hits — we live them, with the road trips, the late-night laughs, the crowd energy, and the heart behind every lyric.
So, Pittsburgh? You crushed it. Who's next?