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Levon Helm's Dirt Farmer album in Woodstock NY

We Are Upstate NY With Music Journalist John Barry on Levon Helm’s Midnight Ramble

By Sal Cataldi | March 28, 2023

When most people think of Woodstock, the first thing that comes to mind is the famous and famously soggy music festival that took place more than 60 miles away in Bethel in August of 1969.

But if you wanted a musical event that best exemplifies the fraternal and altruistic spirit of this small tuneful burg, it would be Levon Helm’s Midnight Ramble.

This series of weekly concerts in the barn home of Helm, the legendary drummer/vocalist of The Band, were born out of desperation – the need to shore up the beloved musician’s finances as he faced bankruptcy, eviction and battled vocal cord cancer.  These were intimate, homespun affairs that attracted an astounding variety of A-list musicians from around the world.

In his new book, veteran music journalist John Barry provides an insider’s look at the history of the Midnight Ramble, something that continues today under the direction of Helm’s renowned singer/songwriter daughter, Amy.  To create this unique backstage history, Barry literally became embedded with Helm. He attended an abundance of Rambles and recorded conversations with the music legend as he traveled to gigs, recorded and hung out with friends and family at his famous barn homestead on Plochmann Lane.

Levon Helm at the Midnight Ramble in Woodstock NY

Photo by Dino Perrucci

Here are some of Barry’s thoughts on this remarkable and still on-going musical event and his two decades-plus living and covering the ever-changing music beat in the Hudson Valley.

We usually begin by asking when or why people came to the Hudson Valley. What’s your story and how did go about becoming one of the key chroniclers of our always-evolving and very fertile music scene?

I came to Ulster County in 1990 to study journalism at SUNY New Paltz. Immediately after graduating, I took a job at a weekly newspaper in Rhinebeck. I quit that job after a year to travel then got hired at The Journal News in Rockland County, where I grew up. I worked there from 1995-2002 and wrote about potholes, planning board meetings and police news; an FBI bribery investigation; the Northern Ireland Peace Process; and the Sept. 11, 2001, terrorist attacks, which claimed nearly 100 local residents who had been in Lower Manhattan that day. The Journal News was part of the USA Today Network, which is owned by the Gannett Company. In 2002, I learned of an opening for a music writer at the Poughkeepsie Journal, another USA Today Network publication. I took the job and remained there until December 2020, when I took a buyout.

Your new book, Levon Helm: Rock, Roll and Ramble: The Inside Story of the Man, the Music and the Midnight Ramble, provides a revealing and emotional look at the final chapter of this remarkable musician’s life and what he meant and continues to mean to Woodstock.  Why are Levon and the Midnight Ramble such an important part of Woodstock’s musical heritage?

Levon and the Midnight Ramble remain such an important part of Woodstock’s musical heritage because of what each illustrates. Levon, in a single instant, stands for all the fame that emanates from Woodstock and the Hudson Valley, the big-time, Grammy-winning, Rock and Roll Hall of Fame, tour bus-rock star stuff. We all love this stuff, me included. But with Levon, it was special because he wanted to share his celebrity with all of us. He wanted us to get a taste of it and we were able to do that at the Ramble because Levon was such an open book with his audience.

The Midnight Ramble remains such an important part of Woodstock’s musical heritage because of its singularity. There had never been any kind of performance like this, where someone of Levon’s stature just opened the front doors of his house and invited his fans in for an intimate performance every Saturday night. And there never will be anything like it, ever again. Levon redefined Saturday nights in Woodstock forever. I mean, you head up to Levon’s house and he plays his heart out for several hours and maybe Chad Smith of the Red Hot Chili Peppers will be there; maybe Donald Fagen of Steely Dan; what about Ricky Skaggs, Bob Weir or Marcus Mumford? Jackson Browne anybody? You’ve GOT to be kidding me.

How and why did the Midnight Rambles begin and what was a typical night like?  How did they grow and what were some of the more memorable nights you witnessed there?

The Rambles were an outgrowth of Levon facing financial calamity. He was in bankruptcy, couldn’t earn a living by singing because he had lost his voice to cancer of the vocal cords and he was facing foreclosure on his home-recording studio in Woodstock, Levon Helm Studios. In true Levon form, the man facing this calamity decides to throw “rent parties” and “go out with a bang.” The live music performances followed, and after a grass-roots start, the crowds started to come. They paid to get in and that continued for nearly a decade. The money raised through ticket sales allowed Levon to keep his home-recording studio and those early performances set the stage for what the Midnight Ramble ultimately became – a highly sought-out musical destination from one of rock music’s iconic performers.

Levon Helm at the Bonnaroo Music Festival

Photo by Ahron R. Foster

How did you get to know Levon and become such an intimate “fly-on-the-wall” who captured his words and thoughts at the Midnight Rambles, in the recording studio and on the road, especially in those long drives to gigs?

Very simply, it started when I began to write about Levon and the Rambles for the Poughkeepsie Journal. I started attending more and more Rambles, and more and more road shows, and I became more of a presence at Levon Helm Studios. I suggested the book, some time passed, then I was invited in to collaborate with Levon on the project. We hit it off and we got along very well. I like to think Levon appreciated my strong work ethic and how I worked very hard to write newspaper articles that were accurate and told the story of the Rambles with texture, tone and a sense of place. Formal interviews for the book were extremely rare. I hung around like a fly-on-the-wall with a digital recorder to capture Levon’s stories, our discussions and anything that might transpire. I transcribed those recordings and used them as the foundation for the book.

I remain grateful to Levon for inviting me to Levon Helm Studios to work on this once-in-a-lifetime project. Working with him altered the trajectory of my life for the better in so many ways. I am also grateful to Levon’s wife, Sandy, and his daughter, Amy, for the many warm welcomes at the studio and for always making me feel at home there. I’m also grateful to Levon’s manager Barbara O’Brien, webmaster Tony LoBue and LHS office manager Geanine Kane, as well as everyone on Team Levon.

A discussion about the Midnight Rambles wouldn’t be complete without talking about what you just called “Team Levon” –  the many folks who gathered around to help him fight eviction and bankruptcy, battle cancer and create this unbelievable stream of musical happenings.

Team Levon was made up of the volunteers who helped launch the Rambles and create a space where Levon could get back on his feet. The members of Team Levon, as well as the Midnight Ramble crew, are without question some of the most authentic, righteous, giving, dedicated and thoughtful people I will ever know in this lifetime. I am thankful to them, one and all.


The Rambles became the impetus for the final triumphant chapter of Levon’s career.  It was a time when he became a Grammy-winning solo artist, the subject of a fantastic documentary and finally stepped out of the shadow of his time in The Band.  I imagine this was a gratifying time for him and all who loved him.

My understanding is that Levon’s “Midnight Ramble Era” was the happiest time in his life.

From your book, it seems that the kitchen was really the place to be when a Ramble concert ended.  Why?

Once the Ramble ended, Levon would head into that portion of Levon Helm Studios where he lived. The crowd would make its way out and numerous people—members of the Levon Helm Band, members of the opening band, guests, members of the media and friends—would head into the kitchen. The kitchen was something of a green room, but it was also so much more. You were in Levon’s kitchen and he would hold court. He would tell wonderful stories about Arkansas and his career as a musician. These were down-home, in-depth stories told with flair and pizzazz that reflected Levon’s passion for stories—hearing them and telling them. This was a guy who, for decades, had told stories in song and in movies. Millions and millions of people have been on the receiving end of Levon’s storytelling. Imagine hearing this guy share a story from across his kitchen table. He would captivate the entire room, which could be bursting at the seams with people straining to hear what was being said. This was one of my favorite aspects of the Midnight Ramble.

Levon Helm on a tracker in Cape May Point

Photo by Chris Howe

For a guy who you say had no use for celebrity culture, he traveled in some mighty glitzy circles at times.  Tell us about the night he introduced you to Jane Fonda.

Levon had absolutely no use for celebrity or fame. He wanted to play music. He wanted to act in movies. He wanted to be paid fairly for both. Levon’s connection with other celebrities came through their shared passion for their craft, be it music or acting. Levon defused all notions of celebrity.

Jane Fonda and Catherine Keener were in Ulster County filming Peace, Love & Misunderstanding, and they attended a Ramble. Jane and Levon worked together years ago in a television movie called The Dollmaker, so they were old pals. In between the set by Phil Lesh of the Grateful Dead and the Levon Helm Band, I was in Levon’s kitchen taking it all in. Levon was speaking with Jane on the other side of the room and I was being a fly-on-the-wall by the refrigerator. He came over to get some ice and said, “John, let me introduce you to Jane Fonda.” My chin hit the floor. Levon took me by the arm, walked me over to Jane and said, “Jane, I want you to meet a good friend of mine.” I remember it like it was yesterday. What a night.

I understand you have a new book on the horizon, one about the many world-class guitarists, in genres from folk and country to jazz, blues and rock, who have called Woodstock and the Hudson Valley home.  Can you give us a taste of what music lovers might expect from this book?

I was honored and thrilled to be invited by Woodstock guitarist and lifelong resident Rennie Cantine, who is also the guitarist in the band Sabrina and the Gems, to work on his upcoming project about Woodstock guitarists. This multi-media project will showcase the many guitarists, famous and not-so-famous, who drew and continue to draw inspiration from the Town of Woodstock. I’m very excited about this. Stay tuned for more.

What is it about the Hudson Valley that makes it unique to live + work here?

The people. My neighbors in the Hudson Valley inspire me every second, every minute and every day. My Hudson Valley neighbors rock, and they rock hard.

Levon Helm clapping and playing at the Midnight Ramble in Woodstock NY

Photo by Dino Perrucci

What impact does your work have on the community?

I like to think that my writing has spurred people to think and act and, in the process, leave a positive impact on the community.

What local businesses do you rely on to be successful, both professionally and to enjoy life?

Terri’s Deli in Uptown Kingston, the Bardavon 1869 Opera House in Poughkeepsie and Ulster County Performing Arts Center (UPAC) in Kingston.

What would be your dream assignment/interview, one that has escaped your grasp until now?

To ride the tour bus with the Rolling Stones, circa the mid-1970s, and write about it for Rolling Stone.

Tell us something about yourself that people might be surprised to know.

I always cry at the end of the movie, It’s A Wonderful Life, when George Bailey’s brother Harry raises his glass and says, “To my big brother George—the richest man in town.” It kills me every time.

What is your favorite non-musical/journalistic activity?

Hiking and camping

Who or what inspires you personally?

People who embrace the challenges of life, no matter how daunting.


Contributing writer Sal Cataldi is a musician, writer and publicist living in the Hudson Valley.

Photos by Dino Perrucci, Chris Howe & Ahron R Foster (Featured)

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Follow John W. Barry on his website


  • Nice article on Levon by John Barry. I am reading his book on the Rambles story now and highly recommend it! From personal experience I can attest that those of us who live in Ulster County are truly blessed with the musical talent that resides here. When you go to the Rambles you feel like part of an extended family. Intimate, and respectful of the history created in that space. My wife and I will be there tomorrow to see Teresa Williams and Larry Campbell, and later on, Leo Kottke. My wife quoted me a statement her grandfather made that went ” Begin with enthusiasm, and end in style.” To me, that is exacted what Levon did, without compromise.

    April 21, 2023
    • inside + out

      Hi Brice, thank you so much for your feedback on this interview and for sharing your comment. That quote absolutely sums up the success of “The Barn” and all those keep the flame alive. Enjoy the Larry Campbell and Teresa Williams show, they rock and there is no better place to see them!

      April 21, 2023

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