Carter & Cleveland on Twin Fiddles & The Watermelon Pickers Festival

In episode 49 of the Music Festivals Podcast, we bring you a front-porch conversation with two of the finest fiddlers to ever pick up the bow, digging into their new album, their long-time friendship and their upcoming show at The 21st Watermelon Pickers' Festival in Berryville, VA.

Jason Carter and Michael Cleveland are each bluegrass legends in their own right, and their new collaboration—captured beautifully on their duo album Carter & Cleveland—is something the genre’s been waiting decades for. These two have been musical friends since the mid-90s, and when you talk with them you can immediately tell that this new twin fiddles collaboration is very close to their hearts.

This episode is a must-see for anyone who considers themselves a bluegrass fan—or anyone who loves hearing how lifelong musical friendships turn into something bigger than the sum of their parts. 

A Friendship Spanning Decades

It all started back in the 90s at a little show in Benton, Kentucky, where Michael Cleveland’s band opened for the legendary Del McCoury Band—Jason’s then-new gig after only four years of fiddling. That brief meeting turned into a decades-long mutual respect, countless festival sit-ins, and now this powerhouse collaboration.

Michael laughed about hearing Jason on a Goins Brothers tape before ever meeting him, saying:

“I was just a kid. This mandolin player hands me a tape and goes, ‘You gotta hear this guy Jason Carter play fiddle.’ And man, from the first time I heard him, I wanted to play like that.”

Their stories are woven with jam sessions under festival tents and impromptu stage invites—moments that ultimately set the groundwork for Carter & Cleveland.

Overcoming the Odds & Chasing the Sound

Michael’s path to becoming the most awarded fiddler in IBMA history wasn’t easy. Born blind and later losing much of his hearing due to infections, he credits the Suzuki method and learning entirely by ear for training him to truly listen.

“I don’t even think about it now unless somebody’s trying to talk to me on my left side,” he told N8 with a grin.

That knack for hearing—and feeling—music is why his band Flamekeeper has won seven IBMA Instrumental Group of the Year awards. It’s also why pairing up with Jason feels so seamless, despite how tricky twin fiddles can be.

“Usually when you get two fiddlers on stage with no rehearsal, it’s a recipe for disaster,” Michael joked. “But with Jason, it’s one of the easiest things I’ve ever done. We approach the music the same way.”

From Kentucky Roots to the Grand Ole Opry Stage

Jason’s story is pure Appalachian bluegrass. Growing up in Lloyd, Kentucky, he was playing guitar at age 8 and fiddle by 15. Just four years later, he landed a dream spot with Del McCoury—kicking off a three-decade run that included being a founding member of the Travelin’ McCourys and snagging multiple Grammys. Our chat took a heartwarming turn when Jason talked about his own “fairy tale” wedding on the Grand Ole Opry stage last October:

“Michael was my best man. We had a sunrise wedding on the Opry stage, then played a set there that night. I mean, how could you top that?”

It was a beautiful example of how deeply these musicians are tied to the Opry’s legacy. Michael described it as “like playing Carnegie Hall... every time you step on that stage, it’s an honor.”

Looking Ahead: The Carter & Cleveland Tour

Their tour this year is peppered with dates across the country, from Maine’s Crooked River Gathering to Kentucky’s Bourbon & Beyond. But one show they’re especially excited for is September’s Watermelon Pickers Festival in Berryville, Virginia.

“Honestly, I’m just excited to get to stand beside Michael again,” Jason told us. “As a fan of fiddle music, to hear that sound coming out right next to you—it’s incredible.”

From stories about first jams in Kentucky, to why the Grand Ole Opry still gives them chills, it’s a feel-good, behind-the-scenes look at two masters of their craft.

Watch the full episode on YouTube or grab the audio podcast wherever you listen—and be sure to check out how to win free festival passes on musicfestivalspodcast.com.  And, don't forget to subscribe!

Ticket Package Drawing for the 21st Annual Watermelon Pickers' Festival Opens Next Week

If you love bluegrass, roots music, and good times with great people, you don’t want to miss this.

I’m talking three days of incredible live music, late-night jams, workshops, and fun for the whole family-plus, kids 12 and under get in free!

Entering the ticket drawing is super easy-just follow the link to the official contest page and throw your name in the hat. Imagine kicking back in the Shenandoah Valley, discovering new artists, and making memories you’ll be talking about for years.

Don’t miss your shot to join us for one of the best weekends of the year. Hit that link, enter now, and maybe I’ll see you at Watermelon Pickers’ Fest 2025!

Next Week: Jesse Shultzaberger from Larry Keel's Electric Larry Land

Next week, don’t miss the start of Season 4 of the podcast with episode 50, featuring drummer Jesse Shultzaberger.

A staple of the east coast music scene, Jesse’s played thousands of shows from jazz to progressive bluegrass, recorded on over 30 albums, and toured Europe—all while mentoring the next generation of drummers. We dig into his work with award-winning flat picker and singer/songwriter Larry Keel, their upcoming studio album, and why Berryville feels like a family reunion.

Don’t miss any of the action—tap Subscribe on YouTube so you’re always in the loop when new episodes, live jams, or fun behind-the-scenes clips drop.

And if you want the good stuff—like giveaways, festival news, and artist stories—sent right to you, jump on our email list. Stick around and be part of the crew, you’ll always know what’s coming up next! 

Festival Performance of the Week:

This week's festival performance of the week really shows off Jason Carter's vocal chops.  The Travelin' McCoury's performance of  The Grateful Dead's "West L.A. Fadeaway" during their show at CaveFest 2024 was absolutely stellar.

The song, featuring lyrics by Robert Hunter and music by Jerry Garcia is a regular inclusion on The Travelers have included this track in their Grateful Ball performances, which showcase their bluegrass interpretations of classic Grateful Dead songs. The song was first performed in 1982 and has since become a fan favorite, characterized by its reflective lyrics and steady groove. I had the privilege of capturing this performance, which took place at The Caverns in Pelham, TN on October 13th, 2024.