My favorite, most poignant memory was from year two. David Grisman was our headliner. I was so excited to meet him when he arrived backstage, but found out that our security team didn’t know who he was and wouldn’t let him in! “Hey, Man! I’m David Grisman, man, your headliner.” But there was another act I was even more excited about. During the planning of the festival in 2005 my best friend Allison Fisher died of cancer. Her band TrueBlue out of Berkeley, CA with husband Avram Siegel, Del Williams and Ed Neff was on the stage (pictured above in 2007).

I had reached out to them to perform again in hopes they would come. They said yes. It was the first time TrueBlue had toured since her death, and their first show without Allison. It was bittersweet but I was so happy they had come. During their set the skies got seriously broody and more and more purple. Then it finally busted open pouring rivulets of rain that streamed down from the sides of the roof. We all huddled in under the canopy top. The show went on and they played to an unphased hearty crowd that donned raincoats and plastic bags. Then, it miraculously cleared and a stunner of a rainbow appeared. I was sure that Allison was there with us, smiling down. Since then it has rarely, if ever rained quite like that during Pickin’. The festival and my many memories take up a gorgeous space in my heart and soul and I look forward to making more for the next 20, if I’m so lucky.
– Julie Sullivan Brace, Pickin’ in the Pines Co-Founder

One of my best memories was of year one in 2006 after we had everything set up for the launch. I watched all the people lining up, waiting to come in. We had a bagpiper march in that year, which added to the excitement and drama. What struck such a deep chord for me, was seeing John Abers and his wife Joan Carstensen walk in with their lawn chairs. John had a big grin on his face. It was really happening, and not just a dream, after close to a year of planning. Julie then later announced by walkie-talkie to our entire crew that the show had actually begun and music rang out from the stage!
– Roger Brace, Pickin’ in the Pines Co-Founder

Heidi Clare & AtaGallop performing at the very first Pickin’ in the Pines in 2006, blending Celtic-inspired music, lively step dancing, and a spirited performance that brought a unique energy to the first festival.

Wow, what a band!…and what a backdrop! But where’s all the onstage foliage, and other fancy decor? Pickin in the Pines has sure come a long way in these 20 short years! Yeah, we were five shaggy Dogboys way back then at the first Pickin’ in the Pines in 2006 (Left to right: Tom Rozum, Chris Brashear, Todd Phillips, yours truly, and Craig Smith). While Pickin has certainly grown and changed over the years, it remains a fantastically fabulous fun-filled fan-favorite family-friendly festival (try saying that five times fast). Chris and I are excited to be back for the 20th.
– Peter McLaughlin

Getting to get up on stage and sing Morning Time with my absolute favorite band (The Brothers Comatose) in 2025 will always be the highlight of my life!
– Deb Hilton

In 2017, Tim O’Brien played in the Commercial building, and took some questions from the fans there. I asked him how his alter ego, Red Knuckles, might sing Bob Dylan’s song “Señor.” He bantered a bit joking around, then sang about 45 seconds of “Señor,” in his Red Knuckles voice – it was quite a hoot! It will always be one of our favorite memories, along with many others!!

– Joe & Teri Falinski

Sam Bush knows and loves his St. Louis Cardinals baseball. Therese and I are Arizona Diamondbacks fans since their inception, and the 2019 PIP gave Sam a chance to drill us on how the Dbacks could possibly trade fan-favorite All Star First Baseman Paul Goldschmidt to the Birds on the Bat. A Goldy MVP Award later, Sam returned to PIP in 2023 to sign our photo from four years earlier and question why the trade hadn’t yielded a National League Pennant. Ironically, the Dbacks earned their second World Series birth a month later.

– Rod Smith

In 2018, Pickin’ in the Pines was honored to welcome Jeff Austin and the Jeff Austin Band to our festival stage. Jeff first performed his own set with his band, showcasing the energy, musicianship, and unmistakable style that made him such a beloved figure in the acoustic music community. For the next set, Jeff joined forces with the Travelin’ McCourys for a very special performance: The Grateful Ball featuring The Travelin’ McCourys & Jeff Austin Band. This unforgettable collaboration brought two incredible bands together for a set of Grateful Dead songs, creating a magical moment that festival attendees still remember. The musicians’ chemistry, the crowd’s enthusiasm, and the shared celebration of this music made it one of those rare Pickin’ in the Pines experiences that stays with you. Jeff Austin passed away the following summer in 2019. We are grateful that he shared his talent, energy, and spirit with our festival community, and we are honored that he was a part of Pickin’ in the Pines.

I brought my aspiring mandolin musician, Juniper, to Pickin’ in the Pines 2025 because of her love for artists like AJ Lee & Blue Summit and The Brothers Comatose. Along the way, she made unforgettable memories, meeting musicians she admires, receiving a hug and high five from AJ Lee, hearing “The Weenie Dog Song” dedicated to her, and meeting Addie Levy before The Brothers Comatose’s set.

Juniper has been playing mandolin for a year and a half and has been inspired by incredible female musicians like AJ, Addie, and Sierra Hull. Moments like meeting Sierra are what make Pickin’ in the Pines so special, the opportunity for young musicians and fans to connect with the artists who inspire them. We love the friendships, memories, and musical connections made at this festival, and we’re grateful for the many musicians who make those moments possible.

– Erin Maidlow

My once in a lifetime chance to sing ” Down Low ” with Town Mountain happened on Friday night in 2024. These opportunities never happen at most venues, it’s one of the best parts of the Pickin’ in the Pines experience. One of the happiest moments of my life.
– Jarrod Lash

As we approach the 20th anniversary, I think about what this festival has meant to my family and our community. My daughters and I have never missed a year. They grew up here, surrounded by music, campground jams, and the friendships that happen in special places like this. Pickin’ has always felt like a family reunion that extends summer just a little longer. Watching my granddaughter, now 2, sit by the campfire way past her bedtime reminded me how important these gatherings are, the music, the people, and the welcoming environment where generations come together. I’m grateful to have been part of this journey from the beginning and thankful to everyone whose hard work has helped create a place where these memories continue to be made.
– Jeff Duncan, Pickin’ in the Pines Campground Coordinator

I’ve enjoyed celebrating my birthday with family and friends every year at Pickin in the Pines. I like to joke that the festival is put on especially for me.
– Dwayne Conn

I had my photo taken with AJ Lee and Blue Summit in 2025. They are such a nice band!

– Bill Johnson

In 2023, Pickin’ in the Pines was honored to welcome the Ronnie Bowman Band to our festival stage. A powerful vocalist, gifted songwriter, and one of bluegrass music’s most respected figures, Ronnie brought his unmistakable voice, incredible musicianship, and warm stage presence for a delightful Sunday afternoon set. From his award-winning years with the Lonesome River Band to his celebrated solo career, Ronnie Bowman helped shape the sound of contemporary bluegrass. His songs have become part of the fabric of the genre, and his influence reaches far beyond the many stages he performed on. Ronnie passed away on March 22, 2026, leaving behind a lasting legacy in the bluegrass community. We are grateful that he shared his talent with the Pickin’ in the Pines family and honored to have been one of the many stops along his remarkable musical journey.

Hot Rize brought more than incredible bluegrass to Pickin’ in the Pines in 2012. They brought a little surprise. Halfway through their set, the band stepped off stage and returned in costume as their hilarious alter-egos, Red Knuckles and the Trailblazers. The crowd was treated to a one-of-a-kind performance filled with great music, humor, and the unforgettable showmanship that has made Hot Rize legendary.

We were thrilled to welcome Molly Tuttle & Golden Highway to the Pickin’ in the Pines stage in 2023. During their set, Molly shared a moment with the audience that many of us will never forget. She removed her wig before performing “Crooked Tree,” the Grammy Award-winning title track from her album. Molly has alopecia, a condition that causes hair loss, and that moment was a powerful reflection of the song’s message: embracing who you are and celebrating what makes each of us unique. Standing on stage with such openness and vulnerability, Molly connected with the crowd in a way that went beyond the music. It was a beautiful Pickin’ moment, an artist sharing not only her incredible songs, but also a personal part of her story with the community gathered under the pines. It is a moment we will never forget.

In 2019, Pickin’ in the Pines was honored to close out the festival weekend with two true legends of bluegrass: Del McCoury and David Grisman. It was a rare gathering of two iconic musicians whose careers have helped shape the sound and spirit of bluegrass.