Rod Serling, the iconic creator and host of The Twilight Zone, made an indelible impact on pop culture. But one of his lesser-known legacies has to be the creation of a Westport institution: if it weren’t for Rod Serling’s stint in Westport in the 1950s, we wouldn’t have Dan Woog.
Yes, it was on Serling’s advice that Dan’s parents moved here when he was three. Serling and Dan’s father, Jim, were friends through Antioch College in the late 1940s. When the Woogs were looking to move somewhere with their two young children (Dan’s sister, Sue, was one at the time), Serling suggested the Woogs purchase one of the new homes going up on High Point Road, where he also lived. "So they paid $27,000 for a house, and the rest is history,” Dan tells Westport Lifestyle.
Most Westporters today know Dan for his unceasing work on his news site, 06880, which is “where Westport meets the world.” Since launching in 2009, Dan has updated the Westport-focused site (which began as a blog, but has almost certainly outgrown that title) daily—often multiple times. “I have not missed a day,” he says proudly. But Dan’s work reporting on and covering Westport goes back nearly as long as he’s lived here. “From an early age, I felt very connected to the town,” he says, describing his childhood on High Point Road as “very Stand By Me,” full of bike rides to Longshore and long days playing with neighbors. “I love history, so I loved learning about where this place came from, back to the 1700s,” he says. In high school, at Staples, he took his appreciation for the town to the Westport News, then a weekly print newspaper. “When I was in 10th grade, I went down there and said to the editor, ‘You know, the senior who is writing the column ‘Up at Staples’ is going to graduate. Can I take it over?’” The answer was yes. Dan wrote “Up at Staples” for the next two years, covering a dynamic time in the school’s history, encompassing anti-Vietnam War protests, Civil Rights demonstrations, top-tier athletics, the storied arts program, and even Staples’ experiment with self-government. “It was a formative experience,” he says. “It taught me how to write, and how to write quickly. I’m very grateful for the opportunity.”
Dan’s byline appeared in the Westport News from 1969, when he was a high schooler writing “Up at Staples,” until his final “Woog’s World” column in 2024—a tenure spanning 55 years. He didn’t originally plan to build his career here in Westport, though. After graduating from Brown University in 1975, “I had no intention of coming back,” he says. But he got a job offer from a psychiatric hospital in Westport called Hall-Brooke to do community relations, and he took it. Shortly after starting, he realized what he really wanted to do was focus on writing. So, from Westport, he launched a thriving freelance career, writing for everything from airline magazines to IBM to locally-based Tauck Tours to more than a dozen books, including School’s Out, a memoir called We Kick Balls: True Stories from the Youth Soccer Wars, Staples High School: 120 Years of A+ Education, and many more. He was also the sports editor at the Westport News, which dovetailed nicely with another role he picked up after coming back: youth soccer coach. “After college, I asked Albie Loeffler, who had been my soccer coach at Staples, ‘Is there a need in the soccer world?’ And he said, ‘We need youth teams.’ So I started one, and very quickly out of that, grew the Westport Soccer Association.” In 1983, he joined the Staples coaching staff as the head freshman coach, and soon added the JV team and served as the assistant coach to the varsity team. He coached 1999 Gatorade Player of the Year Kyle Martino during his Staples career (for more on this, see page TK), and was inducted into the Connecticut Soccer Hall of Fame in 2000. When head varsity coach Jeff Lea stepped down in 2003, Dan took over that role until his retirement in 2022. “It was great. It kept me young, to be a part of kids’ lives and help them not just with soccer, but with all the lessons that sports teaches,” he says. His lessons had a major impact, too: he was named Connecticut High School Soccer Coach of the Year in 2011.
Somehow, amid all these commitments, he found time to launch 06680. “[When I started the site], I was worried about the future of local journalism. I thought it was important, and I still do.” So he taught himself the basics of blogging over a weekend, and debuted the site in March of 2009, amassing subscribers almost immediately. “I had no idea where it was going to go, but there were elements of it that really appealed to me: the interactivity, being able to hear instantly from readers; using multimedia elements to tell the stories; and to be able to write about anything Westport-related,” he says. Seventeen years later, the site is the virtual hub of the town, often breaking news and providing valuable community connection. (That connection translates offline, too, with events like the annual 06880/Westport Downtown Association Holiday Stroll, and the upcoming Soundview Summer Stroll, held in collaboration between 06880 and the Compo Beach Improvement Association, which you can read about on page TK.) These days, Dan starts his morning by doing the bulk of his writing from 5:30 to 9 a.m., takes a break to exercise at the Westport Weston Family YMCA, and spends the afternoon responding to issues and questions in real-time. (If you’ve ever been in the 06880 comment section, you'll know Dan is regularly there, responding to readers.) And Dan loves his daily grind. “People will tell me, 'I just moved here two months ago, and [06880] has really helped me understand my town.’ That’s so gratifying, knowing I helped someone feel at home in a place that has been home to me for so long.”
It might go without saying, but given his wide, varied career, it’s not easy to find a way to sufficiently honor Dan’s legacy here in town. Still, RTM member Andrew Colabella is trying: earlier this year, he launched a petition to name Wakeman B Field in Dan’s honor, which, at press time, had 2,842 signatures. “I was speechless,” Dan says of learning about the proposal. “You know, I was not a great athlete. And nobody goes into anything–whether it's teaching, coaching, or writing—with the idea that they’re going to get rewarded for it, other than intrinsically. But to have people think of me that way…it means more to me than words can express. To be thought of in the same breath as Albie Loeffler, Jinny Parker, Paul Lane, and P.J. Romano, all of whom have fields named after them, is wild.” Maybe it seems that way to Dan, but to nearly 3,000 Westporters and counting, it’s poetic—and seems pretty perfect.
At age 73, Dan shows no signs of slowing down. But it’s easy for him to sum up what keeps him going. “It’s the town, and it's the people,” he says. “And they’re intertwined. The town is in really good hands, and that’s part of what motivates me: I want to let people know what this town was and where it has come from, so that they can take it into the future.”
To read and support 06880, visit 06880.org
“It's so gratifying, knowing I helped someone feel at home in a place that has been home to me for so long.”
"It kept me young, to be a part of kids’ lives and help them not just with soccer, but with all the lessons that sports teaches.”