A new documentary chronicles half a century of iconic photography by Vineyard Haven’s Peter Simon.

Strolling along vineyard haven’s narrow, picturesque Main Street, visitors to the Simon Gallery are often stopped by photos hung in the window. A brooding Jim Morrison. A shirtless Bruce Springsteen. But celebrity alone does not draw visitors through the door: It’s also the way that, in these images, familiar icons seem like friends.

Once inside, gallery visitors gawk at an entire generation inside frames. It might be Joan Baez resting her arm on Bob Dylan’s shoulder, or Jerry Garcia fingering a guitar. And is that the Beatles at Shea Stadium? Martin Luther King framed in light? Robert Kennedy? Allen Ginsberg? John Belushi? Even Lady Gaga and the crowds of Occupy Wall Street?

Is there any cultural crossroad of the last half-century to which Peter Simon did not take his camera?

Most afternoons, Simon sits in his gallery, a slight, unassuming man in a New York Mets cap. Congenial but reserved, he seems to see the world through a lens, even when his cameras are not handy. If asked, he’ll tell the story behind that balcony shot of Led Zeppelin’s Robert Plant, or his huge portrait of Bob Marley, defiant but vulnerable with spliff in hand. But the shyness that first put Simon behind a camera keeps most of his stories hidden inside him. Luckily, his journey is now on a new documentary DVD, Through the Lens: Celebrating 50 Years of Personalized Photojournalism, which traces Simon’s lifelong quest to capture the iconic images of the Boomer generation.

“I wanted a chance to explain my fifty years of work,” Simon says of the three-hour-long DVD, which will be released in summer 2013. “I wanted to get very personal about hang-ups and insecurities, alcohol and recovery, the death of my father, and how that still hurts me. But there’s a lot of joy and celebration in my work as well.”

Simon’s father, Richard, co-founder of publishers Simon and Schuster, introduced Peter to photography. Highly cultured and highly driven, Richard played Tchaikovsky on the family piano and never went anywhere without a camera. When Peter was nine, his father gave him his own camera and showed him the magic to be made in a darkroom. Later on, skinny, buck-toothed Peter found sanctuary behind the lens, and he made friends by handing out the photos he took.

Growing up a Simon, Peter was drawn to music and spotlights. His oldest sister Joanna was an opera singer, sister Lucy has composed music for Broadway shows like The Secret Garden, and then there’s that other Simon sister, Carly—maybe you’ve heard of her. Privilege perhaps, but how to stand out in such a family? “I had these three beautiful sisters, a charismatic mother, a father who died when I was a pre-teenager, and I didn’t know who I was,” Simon says. “Photography gave me a sense of purpose.”

Peter’s talent was quickly recognized. At 15, his photos were published in the widely read magazine Popular Photography. While studying photojournalism at Boston University, his concert close-ups landed him a job photographing for the Cambridge Phoenix (later the Boston Phoenix). An editorial comment in a 1969 issue of the Phoenix summed up his growing reputation: “A lot of people have been telling us that Peter Simon is a genius. We know.”

At the suggestion of a Phoenix writer, Peter sent his photos to Rolling Stone, and at age 22, he received his first freelance assignment for the magazine. Other freelance work took him to the Haight-Ashbury district, to anti-war protests, and to Martin Luther King’s Poor People’s March on Washington, D.C. Absorbed in the idealism and high on the counter-culture—and sometimes its by-products—he captured it all on 35-millimeter film. “It was a very exciting time, and it became my palette of creativity,” he recalls.

But a photographer’s palette needs more than colorful characters. Even the pros struggle to find the defining moment, the perfect shot, but Simon’s work makes it look easy: He seems to have a gift for framing key moments with artful composition. Simon’s celebrity photos typically feature a star onstage before huge audiences, somehow caught in a candid moment of concern or vulnerability. And in his posed portraits, Simon’s genius lies in his own shy, easygoing manner that brings out the best in people. “Peter’s a very touchy-feely guy and he gets people to express themselves that way,” says Ronni Simon, Peter’s wife of 35 years and an artist whose intricate jewelry is featured in the Simon Gallery.

In 1970, Peter followed the call of the back-to-the-land movement. Putting his career on hold, he spent two years milking cows, planting vegetables, and photographing the long hair, flowing dresses, and loving hours on Tree Frog Farm, a commune and subsistence farm he co-founded outside Brattleboro, Vermont. But the eventual disintegration of the farm sent Peter in search of the next step.

Leaving Vermont, Peter bought a small house on Martha’s Vineyard where, like many a Boomer, he began recovering from the 1960s. Over the next decade, he found new interests. A love of reggae sent him to Jamaica where he photographed Marley and other Rastafarians for his book Reggae Bloodlines. He became a disciple of the guru Ram Dass, who ultimately married Peter and Ronni. He resumed his concert photography career, touring with The Grateful Dead and Led Zeppelin and shooting the 1979 No Nukes concerts in Manhattan.

But rock music was losing its intimacy. Writing in his journal in 1984, Peter lamented, “The passion is gone. Artists are in it for the money and the glory…where is the voice of conviction?”

Since the mid-1980s, along with occasional off-island assignments, Peter has turned his lens primarily on the Vineyard, the charms of which continue to enthrall him. The disadvantages of the island, he says, are far outweighed by its pleasures. Year-round life on the Vineyard, he admits, “is not for everyone. Some people have greater mountains to climb, wider bridges to be crossed. But for those of us who enjoy the simple pleasures of life here, there is no other place to live.”

In summer, spring, or deep snow, whenever “the perfect combination of my mood, good weather, and good lighting comes together,” Peter says, he grabs his camera and feels inspired to capture the moment. Peter’s luminescent photographs of Vineyard beaches, ponds, and wildlife add a serene elegance to the music-based photos in his gallery. A dozen of them, ranging from sunsets over Aquinnah to children tiptoeing through the tulips in Tisbury, are featured each year in his Vineyard Calendar.

In 2001, Peter was all set to publish I and Eye: Pictures of My Generation, a coffee-table book featuring his reminiscences and photos. On September 11, Peter had embarked on a publicity tour when he got the news from Lower Manhattan. As the entire country descended into shock, the book received no attention and sold poorly, triggering a personal crisis that spiraled into years-long depression. Peter numbed himself with alcohol, and by 2004, he had checked into rehab in Florida. “If I hadn’t stopped drinking, I’d be dead,” he admits.

In 2008, as part of a personal renaissance, Peter and Ronni opened the Simon Gallery. Inside, visitors can see pieces of his life’s work—an endeavor that, as evidenced by his photographs of the memorial for the victims of the Boston Marathon bombings, is very much still in progress.

Now 66, Peter Simon can smile as he looks back on a life behind the lens. Yes, he did miss one Boomer crossroad: In August 1969, he had tickets to Woodstock, but traffic and booked-up ferries kept him mired on the Vineyard. Otherwise, the photo journey he began by snapping Robert Kennedy’s campaign stop in Riverdale, New York, managed to touch every heartfelt moment of his generation. Simon has often been called “the Forrest Gump of photography,” and he never sold out by seeking the big bucks of fashion or advertising. “I only photographed things I cared about,” he says. “I didn’t know then that the photos would have historic value. It was all very much in the moment.”

Much has been written about the legacy of the Boomer generation—the war protests, the communal experiments, the marches, the music. It truly was a long, strange trip. Peter Simon took the trip. But unlike the rest, he took along a camera, too.

Bruce Watson is the author of four narrative histories and the e-biography Jon Stewart: Beyond the Moments of Zen (NewWordCity).