Alison Stewart was 28 when MTV tapped her to cover Woodstock’s 25th anniversary concert. The network, which was at its heyday in the late ‘80s and ‘90s, wanted a “Woodstock Gets Ready” story that would cover the inevitable antics of the Saugerties show that brought major names like Santana, Green Day, Salt ‘N Pepa, Red Hot Chili Peppers, and Bob Dylan to the Hudson Valley. At the time, Stewart was fairly new to the reporting game. Although she had been with MTV News, first as a producer and later as a reporter, for a number of years, she knew that the Woodstock gig was a big one.
She had to cover it, of course.
“[MTV] really was the most amazing place in the late 1980s and 1990s,” she recalls. “If you were young, creative, plugged in, adventurous, free-spirited, individualistic, risk-taking — it was the place to be.”
Ready to tackle the then-iconic event, Stewart packed into a car and made the drive north to Ulster County with her team. On the way to the hotel, she stopped into Woodstock for food…and promptly fell in love. The charm of the town and of Tinker Street, which reminded her of Circuit Avenue on Martha’s Vineyard before it rose in popularity, called to her, and she couldn’t put it out of her mind.
First though, she had to cover Woodstock ’94.
“It was crazy!” she enthuses. “And so much fun. There was a real spirit of joy and a love of music. This was pre-internet, so people who wanted to be there had to really want to be there.”
Stewart got her coverage at the fest, thereby solidifying herself into MTV’s network at the time. Although she started with MTV News shortly after college as a producer, she switched to conventional reporting to fill a need within the network. In a true case of “right place, right time,” she had the chance to cover the most exciting stories of the era, including Woodstock ’94 and the presidential election of 1992, the later coverage which ultimately won her a Peabody Award.
“I was 25 years old and put in charge of MTV’s first presidential election coverage and was allowed to just go for it,” she says. “I’m not sure that would happen today.”
While she loved the thrill of reporting, she couldn’t deny that it was both a personal and professional challenge. With this in mind, she ultimately made the call to step away from television to return to writing, her true passion. Around that same time, she also made a repeat visit to Woodstock, the quiet town that charmed her from the start. She trekked upstate for a number of years, staying in B&Bs and renting out cars the whole time, before deciding to take the plunge and purchase a weekend home of her own in 1998.
Stewart scored herself a hand-built stone beauty of an abode, which she bought from Rogers Stevens, the guitarist from American rock band Blind Melon. Once settled, she quickly dove into her new track as a writer, hopping back and forth between her Ulster home and her one in New York City, to churn out pages and chapters.
“I would come up for periods of time just to get some quiet and inspiration,” she says of her retreats to Woodstock to write her books. “I think there is something to the idea that the Catskills have some creative magic.”
Photo by Matthew Septimus
That magic must have worked, because Stewart powered through not one, but two books in a matter of years. First up, she dropped First Class: The Legacy of Dunbar, America’s First Black Public High School in 2013. Putting her reporting and writing skills to good use, she painted a vivid picture of the highs and lows of the historic Washington D.C. school. Three years later, she released JUNK: Digging Through America’s Love Affair With Stuff. The topic, which came to her while digging through her late parents’ crowded, stuffed basement, touches upon the themes popularized by hit television shows like Hoarders and Pawn Stars.
The chance to write combined with the reprieve from live reporting was just what Stewart needed to refresh herself and her career. When she made that life-changing decision to focus on writing in 2007, she was already tired of the commercial news industry, which was no longer the field with which she had fallen in love.
“When news became a commodity, something important was lost,” she observes. “The mission of journalism has to fight with the goal of a business, which is to make money.”
Not ready to let go of news altogether, she returned to radio journalism, which she first fell into while in college at Brown University. In no time at all, she carved a name for herself as a radio anchor at outlets like NPR, PBS, ABC, and MSNBC before ultimately taking over WNYC’s “All Of It” for Leonard Lopate.
Nowadays, Stewart splits her time between work in New York City and reprieves in Woodstock. On “All Of It,” she spends her days discussing arts and culture with new and emerging artists in an open environment.
Stewart at Woodstock ’94 / Photo provided by Alison Stewart
“So much media is siloed by political belief, likes, dislikes. I wanted a show that casts a wide net and was welcoming to all kinds of people,” she says. As she and the show approach 600 guests, she reminisces over shared conversations with names like Ani DiFranco, Madeleine Albright, Ethan Hawke, Meg Wolitzer, and Barry Jenkins. While guest appearances are always exciting, Stewart makes a point to never book a guest out of obligation. If they’re on her show, it’s because she wants them on it and she thinks they’ll provide valuable information for her listeners.
She loves her work in radio, to be sure, but she makes a point to keep up with her writing as well. Currently, she’s at work on a non-fiction middle school book and a children’s book — both of which she will continue to tweak until they’re absolutely perfect. Needless to say, she’ll be making quite a few trips back to Woodstock for a dose of that creative magic she discovered so many years ago.