Meet the Deadhead Cyclist

In new book, Boulder Weekly founder shares ‘life lessons on two wheels’ set to the music of the quintessential jam band


In 2017, Stewart Sallo was riding his bike through the calico sandstone Nevada wilderness when his alter ego was born. His feet pedaled to the pulse of a Grateful Dead concert, one of an incalculable number of recordings made over the band’s estimated 2,300 live shows. A scenic wasteland extended all around Sallo as he cycled, truckin’, until he reached the lookout point at Red Rock Canyon National Conservation Area.

“The words ‘Deadhead cyclist’ came to me and it was one of those powerful moments when you knew that you were being guided,” says Sallo, CEO/founder of local alternative newspaper Boulder Weekly. He had enough signal on his phone to check if the domain name “Deadhead Cyclist” was available “Sure enough, it was.” 

Sallo says that’s when spiritual counsel and modern technology collided to put him on the right track. He’d known that he wanted to write a book. In fact, at that point, he already had a few disparate chapters written about life principles that had stuck with him over the years. He bought the domain.

In 2020, in the crush of the pandemic, Sallo set a goal to write one blog post a week, each spotlighting a different concert in Grateful Dead history, set against the backdrop of one Sallo’s more than 200 mountain bike rides a year. He developed a system for picking the best Grateful Dead concert from any given week, then honing in on a lyric that inspired him and riffing off of it, extracting a nugget of truth or a life lesson.

Fifty-two weeks later, Sallo had a catalog of Grateful Dead-inspired wisdom and personal parables that would become his book, The Deadhead Cyclist: Life Lessons on Two Wheels to the Tunes of the Grateful Dead. 

We connected with Sallo to talk about his 185-page translation of The Dead’s deepest lyrics. (This Q&A has been edited for clarity and length.)

How would you describe this book? 

This is not a book just about the Grateful Dead. And it’s not a book just about cycling. It’s a book about life principles inspired by the various passions we engage in. In my case, those passions are the Grateful Dead, cycling and baseball. The main thing I want to get across is that if you live a life of passion and be clear about what your passions are, allow them to guide you, thoughts and words come to you with a certain clarity that should be taken note of. But any passion will do. You don’t have to be a Deadhead and you don’t have to be a cyclist to enjoy this book. 

What are some of the things that the Grateful Dead and cycling share in common?

One of the things I love about the Grateful Dead is that there’s such a focus on nature in their lyrics. One lyric that comes to mind is from the song “Sugar Magnolia”: “We can discover the wonders of nature rolling in the rushes down by the riverside.” It’s when you’re in nature that you really have great access to the wisdom and the deeper meaning of life that can help guide you through troubled times. One of the things I love most about cycling [is being outside].

Do you always listen to live Grateful Dead concerts while you’re riding?

Almost always. Using a certain comprehensive process, I would review all the shows that had been played during that week. And then I would pick the show that I thought was one of the best, if not the best show from that week. Luckily for me, I attended some 200 of those shows. I tried to not pick shows just because I had attended them, but there were a few shows that I had attended that I couldn’t resist naming as [the pick for] “This Week in Grateful Dead History.”

Do you feel like you were cracking the Grateful Dead code through the cipher of their lyrics, or were you cracking the Stewart Sallo code and using their lyrics as a key?

That’s a very interesting question because art is highly subjective. And the Grateful Dead’s lyricist, Robert Hunter, was very reluctant to identify the meaning of his lyrics. Instead, he wanted the listener to develop their own meaning. Which is truly being an artist. Most artists have an idea of what their art means, but understand that their art means something different to everybody. And they don’t want to take that away because art is in the eye of the beholder — or the ear of the beholder in this case. This is one of the things I loved the most about the Grateful Dead’s music: It doesn’t try to answer questions. Instead, it poses questions and provokes the listener to give deep thought to concepts. 

Stewart Sallo founded Boulder Weekly in 1993. He served as publisher for more than 20 years, and today acts as CEO. 

On the Shelf: The Deadhead Cyclist is available on or you can swing by Boulder Weekly (690 S. Lashley Lane) to pick up a copy. Sallo will sign books at the Boulder Bookstore, 1107 Pearl St., on June 29.