A Look Back on 25 Years of Westport Magazine

Take a walk down memory lane with us for our silver anniversary,*… as we travel up Main Street and down the Saugatuck River; across the Playhouse, Players, and Levitt stages; into Weston celebrity living rooms; over to Saugatuck Shores; past the YMCA; into Bedford Square; through Wilton’s downtown; around our schools and libraries; and onto a Remarkable Bookcycle… to see how much things have changed and how much they have stayed the same..

Sept ’98
// Our premiere issue includes coverage of President Clinton’s first trip to Westport for a Democratic National Committee fundraiser at the Inn at National Hall. A $10,000-a-plate luncheon, hosted by Westporters Robert and Yvette Rose, raised $350,000 for the DNC. //

Oct ’98
// James Naughton reminisces about driving down I-95 in the fall of ’76, during a trip back from L.A., and passing “swamp maples just starting to turn red. I cracked the window and got a whiff, just a hint of the beginning of autumn, which is a smell you never get over if you’re raised in the East.” He decided at that moment to move his family here and has been in Weston ever since. //

Dec ’98
// Readers learn “The Lure and Lore of Main Street.” In the illustration: The Gap, Pottery Barn, Lillian August, J. Crew, Oscar’s, Talbot’s, Tavern on Main, Ahorn’s Pharmacy, Simon Pearce, Chase… Within we see the Remarkable Book Shop, the inspiration for Jane Green and Ian Warburg’s Remarkable Bookcycle—a mini mobile free library, unveiled at Compo Beach 20 years later. //

April ’99
// Jane Kendall’s “The Hollywood East” lists the stars who lived here long before Shonda Rhimes and Scott Foley came to town: cowboy star William S. Hart, Lillian and Dorothy Gish, David Wayne, Joanne Woodward and Paul Newman, Eva Gardner, Arthur Kennedy, Marlo Thomas and Phil Donahue, even Elizabeth Taylor. The Man in the Gray Flannel Suit, with Gregory Peck and Jennifer Jones, featured scenes of Main Street. Gene Tierney grew up on Clapboard Hill. //

June ’99
// The cover features 17-year-old twins Tyler and Cameron Winklevoss rowing on the Saugatuck River. In 2004, the twins would sue Mark Zuckerberg, claiming Facebook was created from their idea. They settled for $65 million. They would row for the U.S. in the 2008 Beijing Olympics. //

July/Aug ’99
// “Will the Westport Country Playhouse Survive?” David A. Rosenberg writes about the icons, from Tallulah Bankhead (1941), who appeared on its stage and laments the shift away from theater to movies and sporting events. Carole Claps comments, “It’s got the makings of magic, but the magicians have left town…. But what a great thing if we can save the Playhouse and bring it into the next millennium, if we can resurrect it from the ashes.” Cue Newman/Woodward. If only we had that dynamic duo today, as a Save the Playhouse campaign kicks off. //

Nov ’99
// Songwriter, guitarist, disco legend, record producer Nile Rodgers recounts how 20 years prior, when he moved to Saugatuck Shores, the neighbors weren’t so sure about a Black man with dreadlocks moving into the neighborhood. He was undeterred. Rodgers contentedly settled in and enjoyed frequenting Westport’s Commuter Coffee by the train station (which closed, in 2018, after 42 years). Twenty years before George Floyd was killed, Rodgers comments, “There’s one thing in this country that every black person knows. It doesn’t matter if you are Oprah Winfrey, Michael Jordan, Bill Cosby or…Nile Rodgers. You’re a target since you’re black. What we all have to learn is you can’t fix the sins of the past by beating up on people.” //

Jan 2000
// The Millennial Issue: Green’s Farms School is under renovation and “a 190,000-square-foot structure on a one-hundred-acre campus next to Staples High School”—Bedford Middle School—is under construction. James Lomuscio predicts: “You are sure to see more knockdowns to erect starter castles, more pejoratively referred to as McMansions.” He adds: “Who’s to say these changes are bad. Yes, the downtown bookstores are gone, but the town’s long love affair with the written work has never been stronger. Look at the new, recently remodeled, massive Westport Public Library…. More books circulate with regularity there than at any other public library in the state.” // Just wait for the $20 million renovation 20 years later. //

March 2000
// Peggy McCarthy asks: “Is the town assuming a facelift for the new millennium, or is it losing its identity?” Debby Angotti, owner of houses dated 1707 and 1711 on Old Hill Road, comments, “I think builders have done a lot of damage recently to Westport. I think it’s really left an indelible mark. It looks much less like New England than it used to.” // Rosenberg’s “A Class Act” celebrates Staples Players, from star starts on that stage to the production of Pippin that went to Edinburgh’s Fringe Festival (one per state was chosen). He writes about “Ann Sheffer, a member of the committee that issued the 1997 report ‘Creative America’ to President Clinton. Among its recommendations is integrating the arts in education because ‘a society that supports the arts and the humanities…is assuring the conditions of its own flourishing.’” Sheffer says, “My lifelong love of theater started with the Players.” // She was honored with a Light a Fire Award in 2013 and continues to advocate for the arts today. //

June 2000
// “Westport director Mark Gentile hits the jackpot with the most popular game show ever, Who Wants to Be a Millionaire.” The ABC quiz show starred Regis Philbin, Gentile also won a Daytime Emmy for directing The View. //

Sept 2000
// “Does affluent suburbia pose too many pressures for young people?” Peggy McCarthy’s article opens with “fourth-grade girls on frantic diets … some even taking overdoses of Tylenol because they are depressed about their bodies. Middle-school children hooked on drugs and alcohol, or engaging casually in oral sex…” // This was before smart phones and social media. No surprise that our 2022 eating disorder story reports a rise in cases. A support group at Staples for teens who want to quit smoking is mentioned (now we need one for vaping). Therapist Linda Keller advises: Assign chores “so they feel they are contributing and integral members of the family.” // Next up: “From hardscrabble and humble beginnings, Westport’s Gault family has maintained a business dynasty nearing the sixth generation.” Roseann Spengler’s story begins: “Brendan Donaher loves trucks. Not unusual for a seven-year-old boy. But what is different about this Westport youngster is his fascination with oil trucks (real ones), machinery and tools. ‘He couldn’t care less about TV or Pokemon,’ says his father, Jim. Brendan often wears work clothes and work boots… His Saturdays are spent with the men in his family at their local business.” Brendan is the grandson of William Leonard Gault of L.H. Gault & Son—in business in Westport for 113 years. // Another story explores “Growing Pains and Gains” in Wilton. // A sailing piece set at the one place that seems to withstand the gale-force-wind pressure to modernize — the Cedar Point Yacht Club — gives readers a breather. //

Oct 2000
// “Joanne Woodward’s New Stage of Life.” She “began on small Southern stages” and “has come full circle on small New England stages, both as an actress and a director,” writes Timothy Dumas. “She now spends most of her public energy rejuvenating the Westport Country Playhouse where she and Paul Newman starred in A.L. Gurney’s Ancestral Voices in July.” //

Jan 2001
// “Silicon Valley we’re not. But that doesn’t mean that dot-com entrepreneurs, like yesteryear’s forty-niners, aren’t mining our region for the next bonanza.” // Diane Benson, who had her son set up a website for her sports-medicine business because no VC would invest otherwise, says: “The venture community was investing in companies that were run by kids—and that was one of their criteria.” $16 million came in, and $3.6 million had been invested in her e-commerce when the bubble burst. //

June 2001
// “Lyme disease: A Plague of Uncertainty.” The Westport-Weston Health District declares: “Would you take action to protect your family from the Ebola virus or mad cow disease? Yet everyone with a yard in Fairfield County is in far more imminent danger from the little ol’ deer tick.”//

Sept 2001
// “A Preschool Primer” lists some of the beloved preschools we will cover again in 2022: St. Francis of Assisi Preschool, Green’s Farms Pre-School, Westport-Weston Cooperative Nursery School, Landmark Academy, Wilton Montessori… //

July/Aug 2002
// David A. Rosenberg reports on longtime Westonite Christopher Plummer, who narrated The Outlivers film to honor Weston’s bicentennial in 1987. “This year he did a benefit titled ‘A Word or Two Before You go’ for Westport Country Playhouse.” About preparing to play the daunting part of King Lear at the Stratford Shakespeare Festival, Plummer says, “I’ve got to enjoy King Lear. That’s going to be the most difficult thing to do. Not to play it, but to enjoy playing it.” //

Jan 2003
// “Joe Pantoliano: The Villain in the Village. The Sopranos bad boy Joe Pantoliano starts anew with a revealing memoir, a hip SoNo restaurant, hot movie roles…and a house by a pond in Wilton.” // Our last issue recommended seeing him off-Broadway in Rock & Roll Man. //

Feb 2003
// Joe Barrato — on the list of the most powerful people in menswear, the longtime CEO of Brioni USA — was named one of the “ten best dressed men in fashion” by Esquire. He dressed everyone from Robert De Niro to Nelson Mandela and graduated five kids from Staples. “He has a bone-deep belief in the intrinsic quality of a tailored garment,” says Jack Mitchell, CEO of Mitchells. // How many still do in the post-pandemic age of working from home? //

May 2003
// “Victim or Villain? Martha Faces Her Perfect Storm.” Timothy Dumas asks: “Sure, she strikes fear in the hearts of her employees, is facing allegations of insider trading and has managed to alienate herself from the better part of Westport, but is she really all that bad?” // She just appeared on the July/Aug 2023 cover, proving it’s never too late to reinven yourself. //

Sept 2003
// “Special Delivery: All the options for better births.” The national C-section rate is at an all-time high of 25 percent. I’m pictured with baby Jamie (the first of a few appearances in the magazine for the future actor/dancer). I switched from a doctor at Yale to a midwife at the birth center at St. Mary’s Hospital in Waterbury, as a result of my research for this story. // Westporter Cynthia Overgard’s podcast “The Down to Birth Show,” covered in 2020, is needed more than ever, with the Cesarean rate up to 32 percent. //

July/Aug 2004
// “He’s sold 52 million albums worldwide, raised $4.5 million for the charity that bears his name and yet Westport’s Michael Bolton says he’s just a regular guy.” Suzanne Gerber covers Bolton’s working-class childhood in New Haven and his passion for giving back: “MBC has been working with the Yale Child Study Center in New Haven. Together they’ve conducted important studies on homelessness, funneled money to women and children in need and created a safe space for kids from violent homes and neighborhoods.” // Bolton stepped in at the Levitt when Ray Charles injured his hip and cancelled. He then offered to put on a concert to kick off the Levitt’s renovation campaign. //

Sept 2004
// “Jared Cohen: How a Weston High grad went on to become an author, explorer, Rhodes scholar and Washington confidant.” Writer Timothy Dumas predicts: “He’s on his was to someplace big.” // He made Time’s 100 Most Influential People list in 2013. //

Dec 2004
// Gary Santaniello reports, “When Jane Green burst upon the British literary scene back in 1997, her novels were like a hot new nightclub.” A year later, she discovered Westport: “I mean, I just came here for an hour six years ago and stepped onto Main Street and said, ‘Home.’” // “She talks with relish about getting her coffee at Doc’s Cafe on Riverside Avenue.” Doc’s was demolished in 2011. Green must have found another source of caffeine because her book tally — then 7 books in 7 years — has reached an astonishing 21. //

Feb 2006
// “The Evolution of Downtown.” Writer Bill Slocum ponders, “Is the fabled ‘Golden Half-Mile’ getting too glittery for its own good?” Gordon Joseloff reminisces about biking to the YMCA to watch Saturday cartoons and leaving bikes on the bike rack. “You never worried about anyone stealing them.” David Waldman chimes in: “I see it as a positive transition… People want to live here, and they feel Main Street gives them an exciting type of Rodeo Drive-thing.” // Waldman’s beautiful Bedford Square delivers just that ten years later. On a wintry night, a walk through it feels like a stroll through a fairytale, with nary a bike thief. //

Dec 2006
// “When Westport Loved Lucy.” The intro sounds like 2020: “The demographic tide flowing outward from New York City was in full flood, with Westport receiving its fair share of urban refugees.” But it was the 1950s and even the Ricardos of I Love Lucy moved to Westport, in the hit show’s final season. A favorable report from a senior writer “convinced the I Love Lucy brain trust that instead of using a fictional town name, they should go with the real and very charming Westport.” // “Charming” would not fit our town’s depiction in the 2016–2021 sitcom, American Housewife. //

Jan 2007
// “Collector’s Edition: 40 People Who Created a Lasting Legacy.” We cover early settlers — Roger Ludlow, Thaddeus Burr, Ebenezer Jesup, Horace Staples — to Edwin Mitchell, the Sheffers, Paul Green, Paul Newman and Joanne Woodward. //

Sept 2007
// James Naughton becomes a champion for Wildlife in Crisis, founded in 1989. // Visit the Westport Front Porch Facebook page to see this is still where locals send those needing help for an injured bird or orphaned fawn. //

Sept 2008
// Collector’s Edition —10-Year Anniversary. Mitchells, meanwhile, celebrates 50 years of style. // “In a 30 Under 30,” Justin Paul, age 23, is named “Most likely to be on Broadway.” // His smash hit Dear Evan Hansen would open in 2016 and win six Tony Awards, including Best Musical. //

Nov 2008
// Paul Newman passed away in September 2008, just as we featured his Hole in the Wall Gang camp for ill children. Newman lived here half a century. Chef Michel Nischan, his partner in the Dressing Room restaurant at the Playhouse then, asks: “What can we do to pick up the flag and all be Paul?” //

March/April 2011
// The annual State of Real Estate reports glimmers of hope: “incremental yet steady recovery back from the depths of recession.” The commercial real estate report airs concerns about downtown Westport’s “mallification.” //

Jan/Feb 2013
// Melissa Joan Hart and baby No. 3, Tucker, grace the cover. The Hollywood star moved here a few years prior, lured by Westport’s small-town feel. “It’s a real community. It’s what I dreamed of,” she says. // The family relocated to Nashville during the pandemic. //

Sept/Oct 2013
// The 15-year Anniversary Issue is heavy with a feature on teacher Kaitlin Roig protecting her first-grade students during the massacre at Sandy Hook Elementary School. //

Nov/Dec 2013
// Westporter Connie Silver graces the cover. Silver went from poor child in Maine to AIDS activist and donor behind NYU’s Silver School of Social Work: “She was the one who hugged AIDS patients when their own mothers wouldn’t.” // James Naughton wins the Light a Fire Lifetime Achievement Award. //

May/June 2015
// “Women Rock.” Because so many women in our towns do. Included are the fierce females behind Dream Spa, She La La, The Granola Bar, JL Rocks and Lera Jewels. //

Sept/Oct 2015
// Chris Hodenfield interviews Pulitzer-Prize-winning photojournalist Lynsey Addario about covering conflicts in Iraq, Afghanistan, Sudan and Syria. // The Common Core hits our schools. Darcy Hicks comments on the arts and empathy being pushed out of the curriculum: “Writing is now more formulaic, dry and impersonal than it was when students were writing from the heart, as imaginative, authentic children with worthwhile stories to tell.” // Just wait for AI. //

Sept/Oct 2016
// “Raise the Curtain” details the history of Staples Players, founded by history teacher Craig Matheson and talented student Christopher Lloyd (Taxi) in 1957. “Matheson recounted that in one evening watching TV, he and his wife once spotted seven Players alumni.” Notable recent Players: Adam Kaplan (The Big Leap), Clay Singer (The Band’s Visit Broadway tour), Brittany Uomoleale (“Britt Baron” – Glow), Alisan Porter (The Voice Season 10 winner), and of course Justin Paul. //

March/April 2017
// “The New Downtown: Over ten years in the making, David Waldman’s Bedford Square is ready for business.” //

Sept/Oct 2017
// Justin Paul and Benj Pasek — the musical geniuses behind Dear Evan Hansen and La La Land — grace the cover. “Back when he was a kid at Long Lots Elementary School, Justin Paul loved the mallet percussion set in the back of the music room. He remembers playing and improvising during music class, a regular part of the curriculum in Westport. Imagine if he grew up in one of the many districts where music has stopped playing, where math, informational text and standardized test prep fill the day with the dull sound of No. 2 pencils on paper. It’s unlikely this Westport native would have taken the stage to receive an Oscar and a Tony this year, with a Grammy and an Emmy as possibilities within the next.” // As predicted, in 2018, Paul nabbed a Grammy. //

May/June 2018
// “Nearly 1 in 4 youths, ages 13 to 18, are suffering from anxiety. Our teens have had enough.” The article outlines a brew of high expectation and emotional frailty. “The uphill suicide graph correlates eerily with the introduction of the iPhone.” //

Sept/Oct 2018
// The 20th Anniversary Issue looks at superstars who came of age while the magazine did: actors Abby Elliott, Adam Kaplan, and Alisan Porter; soccer player Kyle Martino; foreign policy expert/biz wiz/bestselling author Jared Cohen. //

May/June 2019
// On the cover, Bill Mitchell and Andrew Mitchell-Namdar represent Mitchells, winner of Men’s and Women’s Fashion in our Best of the Gold Coast annual issue. //

May/June 2020
// “A New Day: Let’s talk about who we are and what we love about our community.” This pandemic issue features drool-worthy food from the Whelk, dream beds at Serena & Lily, rockin’ JL Rocks rings, Inn at Longshore weddings, JoyRide workouts… The word must have spread; the influx to our area began soon after. //

Nov/Dec 2020
// “Real Heroes: Stories of COVID-19. Anyone who has been through a major disaster will tell you, it takes a community.” Our Light a Fire winners are an especially brave
bunch in 2020. //

Jan/Feb 2021
// Readers get Nile Rodgers on the super-sized houses in Saugatuck Shores: “Rarely do Westport old-timers wander the formerly cottage-lined streets of their shorelines neighborhoods and compliment new-fangled palazzos that have taken their place. But if Rodgers has mastered anything in his life (what he has mastered is too long to list here), it’s how to stay current.” His We Are Family Foundation is evidence of another local celebrity with a super-sized heart. //

May/June 2021
// When Christopher Plummer died at 91, he was eagerly preparing to play the lead in King Lear on-screen, proving he triumphed over his 2002 trepidation about the role. // Patty Haberstroh’s family succeeds in getting June 2 declared Lou Gehrig Day. Patty, with Westport’s Department of Health and Human Services for 20 years, was diagnosed in 2017. // “The Mann Clan actors find the silver lining — and silver screen — in 2020.” //

March/April 2023
// “Christian Siriano finds a home for himself and his store, The Collective West, in fashionable Westport.” He brought Fashion Week to his backyard during the pandemic. // In May he hosted a dreamy Pink Aid benefit show at his store, drawing stars like Whoopi Goldberg and Rosie Perez. //

May/June 2023
// Samantha Yanks — former EIC of Hamptons and Gotham, curator of The Connecticut Edit— introduces herself as our new editor. //

Should I Stay or Should I Go?

Do you think Westport/Weston/Wilton will always be your home?

Eduardo Andrade

Georgetown Student
Westport: 2002 to Present

“It will always feel like home, but I don’t plan to stay in the region. The extreme pre-collegiate nature of Staples encourages students to look outward toward the future; that’s what I believe this town has designed us to do.”

Charlotte Glick

University of Michigan Student
Weston: 2003 to Present

“Weston’s small-town wholesome vibe, close-knit community, interconnected school system and backcountry feel will always be my inner-child happy place. No matter where I go in life, when I return to Weston, my heart is happy and I am home.”

Natalia Mann

Staples High School Student
Westport: 2009 to Present
“Yes, I eventually want to raise my family here. It is such a fun place to grow up!”

Ava Coughlin

Cider Mill School Student
Wilton: 2014 to Present

“Yes! Wilton will always be my home because all of my friends and family are here.”

Maddy Edwards

Fordham Student
Westport: 2003 – Present

“A lack of ethnic and economic diversity may deter me from raising a family here, but I will always have fond memories of my childhood growing up in Westport.”

Why have you made Westport/Weston/Wilton your home?

Joe Pantoliano

Wilton: 1999 – Present

“The setting of our home is so calming with the pond and the trees. Also, the lifestyle is much more relaxed than being in Los Angeles. It’s wonderful to wake up and not have to see any humans—just our puppies.”

Andrew Wilk

Westport: 2006 – to Present

“We chose to live in Westport because of its wonderful school system, proximity to the water, basketball hoops in every driveway, and very important to us: Westport is an Arts Forward community.”

Lowrie Gibb

Retired (Financial Services)
Westport: 1968 – Present

“It was by chance because I was transferred here, and I’m not going anywhere! This place is perfect for me—I love going to the beach, Old Mill Pond, and visiting my four-legged and two-legged friends in Winslow Park daily.”

Jara Landon

Founder of Poshmom.com
Weston: 2002 – 2023 (moved to Westport in June)

“We moved here in 2002 much to the dismay of family in New York. We just couldn’t see raising a family any other place once we laid eyes on that child-filled playground at the beach on an abnormally warm November day.”

Dan Woog

Westport: 1956 to Present

“We pack a lot of amazing people, beauty, arts, great restaurants and fun into 33 square miles.”

Emeka Enu

Pharma/Business and Children’s Book Author
Wilton: 2020 to Present

“I love Wilton because of the people, the great school system, and because it’s a small town close to a big city!”

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