Westport, CT August 2026

JAY MANUEL

ON HIS 15 YEARS IN FAIRFIELD COUNTY: "THIS WAS A PLACE FOR FAMILY"

A Community Built on Family

If summer had a last call, August would be it. It’s the month of squeezing in one more beach day, one more weekend getaway, and as much family time as possible before the routines of fall return.

That feeling is at the heart of this month's Family, Kids & Pets issue.

Our cover story features television personality Jay Manuel, who is selling his Fairfield County home. While many know him from his television career, our conversation centered around something much more personal: home, family, and the memories that stay with us long after we leave a place behind.

The issue also shines a light on some impressive young people in our community. We meet Staples student Emme Dorfman, whose Dogport initiative is advocating for a fenced dog run in town. We also explore ways families can support student-athletes as they balance academics, sports, and everything else that comes with growing up.

Of course, no family issue would be complete without our four-legged family members. You'll meet local dogs whose roles extend beyond companionship and learn about the beautiful custom pet portraits created by local artist Missy Greenberg.

As many families begin planning for the years ahead, we also spoke with local financial professionals about saving for college and preparing for future educational expenses.

And before summer officially comes to a close, we've rounded up several driving-distance resorts that make for an easy end-of-season getaway without the hassle of air travel.

As always, our Editor's Pick wraps up the issue with another favorite from right here in our community.

Thank you for reading, supporting our local businesses, and helping make this community such a special place to call home. I hope you enjoy the issue and make the most of these final weeks of summer.

Warmly,

August 2026

PUBLISHER

Marisa MacLean | marisa.maclean@citylifestyle.com

EDITOR

Sara Gaynes Levy | sara.gayneslevy@citylifestyle.com

CONTRIBUTING WRITERS

Elizabeth Ginns Britten, Jennifer Wider, MD

CONTRIBUTING PHOTOGRAPHERS

Bevy Rutledge, Brook Road Photography

Corporate Team

CEO Steven Schowengerdt

President Matthew Perry

COO David Stetler

CRO Jamie Pentz

CoS Janeane Thompson

AD DESIGNER Rachel Chrisman

LAYOUT DESIGNER Rhiannon Coffman

QUALITY CONTROL SPECIALIST Megan Cagle

MARISA MACLEAN, PUBLISHER @WESTPORTLIFESTYLE

Lifestyle’s

print + digital packages, your business captures attention wherever our community is looking. Build unmatched local credibility on the page, and drive immediate action online.

city scene

honoree Robin Jaffee Frank and past honoree Lewis Derogene,

and Penny Yi.

Westporter Wins The World of 8 Billion International Student Video Contest

Katherine Rose Li, a sixth grader at Westport’s Bedford Middle School, won first place in the World of 8 Billion International Student Video Contest sponsored by Population Connection. Her 60-second video,  Hanging by a Thread ,  tackles the environmental challenges created by fast fashion and proposes the use of biodegradable fabrics in clothing production as a key to a more sustainable future. To see Katherine's video and learn more about the organization, visit worldof8billion.org

Loews Philadelphia Hotel Launches Fun Stuff For Kids

Taking a road trip to Philly? At the Loews Philadelphia Hotel, kids can check out Loews Little Legends STEAM Explorer Kits to use binoculars, compasses, magnifying glasses, and kaleidoscopes to observe, experiment, and uncover new perspectives around the city. Also, on the last Sunday of July and August, at the hotel’s monthly art and jazz brunch,  find a kids' art activity inspired by the featured artist from Morton Contemporary Gallery.  loewshotels. com/philadelphia-hotel for more

A Smarter Move Starts Before Fall

Summer in Westport is a time to recharge, reconnect, and plan ahead. While the market naturally slows in July and August, savvy buyers and sellers use this time to position themselves strategically for the fall market.

With deep local insight, trusted relationships, and conciergelevel service, Erica helps clients navigate each move with confidence and discretion whether preparing to list, searching for the right opportunity, or exploring off-market possibilities.

The Levitt Pavilion Gives 'Em Something to Talk About

13-time Grammy-award winner and member of the Rock & Roll Hall of Fame Bonnie Raitt is headlining the Levitt Pavilion's annual gala on August 9th! All tickets include chairs. Tickets, from $365 for concert only, and $505 for the cocktail party at Massi Co. and Walrus Alley + the concert, at levittpavilion.com

Photography by Gray Peak Images

& Asanas Animals

FOR YOGA CLASSES WITH KITTENS, BUNNIES, AND PUPPIES, LOOK NO FURTHER THAN BREATHE2FLOW.

PHOTOGRAPHY BY TAYLOR LUCATINO AND MADELINE ST. AMOUR.

Animal lovers know what a relaxing effect a furry friend can have. It’s exactly why Lindsay Riley created Breathe2Flow last year, a Connecticut-based pop-up yoga series that features animal companions. “After COVID, when I started teaching [in-person] again, I just thought I want animals,” Lindsay, who has been teaching since 2019, tells Westport Lifestyle. She partnered with Everybunny Counts, a local rabbit rescue in Ellington, to offer yoga with rabbits, with proceeds benefiting the organization. “They became really successful classes,” she says. “So then I thought: what other animals can I use? Who else can I help?” She added a class with a kitten rescue, as well as one with French Bulldogs from a nearby owner. Breathe2Flow has been popping up with animal yoga all over CT ever since, from Stamford to Fairfield to Central Connecticut, including private classes by request (Yes, she will come to Westport!).“I know that

“DO WHAT FEELS GOOD. AND IF WHAT FEELS GOOD IS PETTING A CAT, DO THAT.”

when I am with animals, I’m always so much more relaxed. To combine that with yoga, an already-calming environment, just really spoke to me,” she says.

One thing Lindsay really loves about having animals in the room is how accessible it makes yoga practice, for people of all levels and abilities. “It’s great for beginners, because it breaks them out of feeling like everyone is looking at them,” she says.

“I always say, if you don’t want to practice any yoga, that’s fine. You can go at your own pace and do what feels good in your body. And if what feels good is petting a cat, just do that.”

It’s also become a meaningful way for Lindsay to give back.

“I had a rabbit when I was younger, Bunzy, and he was my soul rabbit,” she says. “I feel really strongly about giving back to Everybunny Counts rabbit rescue, because I know how good they are at caring for the animals, and I want to be able to

give them as much as I can.” To date, she’s held 125 events and raised more than $4,000 for local animal rescues. Many of the animals in her classes are available for adoption, too, and are often taken home by charmed classgoers at the end of the session. “It’s a great way for people to meet the animals,” she says. “Sometimes a kitten will choose one person and stay on their mat the whole time. That usually means they’re getting adopted by the end!”

The best part, she says, is seeing someone blissfully calm during the closing meditation, content with an animal on their chest. “Honestly,” says Lindsay, “I’m living my dream: doing yoga and working with animals.”

For more information or to book a class with Lindsay, visit breathe2flow.com

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JAY MANUEL’S

CONNECTICUT HAVEN

THE TV PERSONALITY OPENS UP TO WESTPORT LIFESTYLE ABOUT LEAVING FAIRFIELD COUNTY AFTER 15 WONDERFUL YEARS.

ARTICLE BY SARA GAYNES LEVY

“The idea, really, was to have a place for my whole family to get together,” Jay Manuel, the television personality, best known as the creative director on 18 seasons of America’s Next Top Model, tells Westport Lifestyle of his decision to purchase a home in Wilton nearly 15 years ago. “My sister lives on the West Coast, my parents lived in Toronto [his father sadly passed away earlier this year], my friends are all still in the city. I always felt like it would be great to have a place where everyone could stay and have their own space.” But when he bought the nearly three-acre property in 2011, he had no idea how special the home would become to him. “There’s such a serenity and a calm here. This is such a great place to be.”

If it’s news to you that Jay has been our neighbor for so long, you’re not alone: one of the reasons he was originally drawn to the Wilton home was the seclusion it afforded. “I’ve never really posted from within my home,” he says. “I wanted to keep it private, as a place for my friends and family.” But now, Jay has made the difficult choice to sell the house. “It took me a long time to get to this decision, but the things I’m working on now are going to keep me away,” he says. And he’s ready to talk about his life in Fairfield County, and how much it has meant to him. “[Before moving to Wilton,] I spent 21 years in Manhattan,” he says. “And I had a weekend

home in the Catskills. Because of my schedule, I travel a lot, and I noticed I was coming home to the city, dropping my bags off, getting in the car, and driving three-and-a-half hours upstate. I thought there has to be a middle ground that makes more sense. I was really trying to find a balance in my life.” As soon as he saw the home in Wilton, he knew he’d found it. The stunning, tree-enclosed 2.75-acre property is surrounded by protected wetlands. “I loved the privacy,” he says. “The energy was just so special.” Add a flat 50-minute commute to Midtown, and he’d found the balance he was looking for. “You can be so close to the city, but feel like you’re a world away. I knew this was an opportunity to build something that could be like an oasis. It just felt right.”

Jay was something of a pioneer among the growing population of fashion and entertainment industry vets who now call Fairfield County home. Over the years, he customized features like a heated saltwater pool, outdoor kitchen and living area, and a standalone 800-square-foot gym. He added space, taking the house from four bedrooms and three-and-a-half baths to five bedrooms and four-and-a-half baths. “I entertain a lot, and I started having dinner parties. I remember Christian Siriano coming over, and he was like, ‘oh my god, I didn’t realize you could have this kind of space here.’ And now he lives 12 minutes away!” He’s loved witnessing the boom of the Fairfield County dining scene, counting Westport’s Dandelion, Southport’s Artisan, Fairfield’s Esh, and Redding’s Wire Mill Barbecue among his favorites. “The food is amazing here,” he says. “It rivals the city.” (He also enjoys a good walk-and-shop in downtown Westport.)

More than anything, Jay says his time in Wilton was a haven for his creativity. He wrote his debut novel, 2020’s The Wig, The B*tch, & The Meltdown , from his Connecticut home. “I loved writing in my

office every day—the energy out here allows my mind to be super creative,” he says. “When you write fiction, everything comes from you—you are every character. So I got to know myself in a very different way.” When he needed a break, he’d take his two Isabella Dachshunds, Neo and Bella, out for walks around the backyard. “Walking my property always feels so restorative, but also allows me to stay in my creative headspace.”

Jay had always wanted dogs, but felt a pet wasn’t a great fit for his life in Manhattan. He got littermates Neo and Bella, now 13, just a year after he moved, and they love the expansive yard, paths, and pool area. “They are my light!” Jay says.

With so many memories, it really is hard to say goodbye. “It was a place to connect,” Jay says. “My father loved it here. This was the central gathering place for my family, with a big dining room to host Christmases and Thanksgivings, where everyone could be around the table.” Whatever’s next, Jay will always hold a place for his time in Fairfield County. “It has been a huge part of my own mental health while juggling this business,” he says. “Even if you’d had a rough day, you just got this sense of calm and beauty here.”

For more information on the property, visit sothebysrealty.com or seetheproperty.com/ story/487191/b

A life , Guided by thoughtful wealth management. well lived

You have built a remarkable life shaped by vision, perseverance, and thoughtful decisions. Your wealth should be guided with that same intention.

Welcome to Dogport

Last year, 17-year-old Staples student Emme Dorfman wrote a speech for a “local persuasion” unit in her rhetoric and persuasion class about an idea for a fenced-in dog run somewhere in Westport. “I have two dogs, Bode and Ozzie, and they love to run around and play, but it’s hard to let them off leash,” she tells Westport Lifestyle about the inspiration for her speech. Her teacher loved the idea, as did her parents. “We thought, why don’t we see what it would take to actually make this happen?”

One of the best things about Westport is our willingness to embrace civic participation from residents of all ages. “I know a lot of high schoolers have things they want to change, but they sometimes think it’s never going to happen,” says Emme. “I think it’s awesome that Westport listens to the youth—we want to improve our town, and we’re the next generation.” With that in mind, she got in touch with members of the Parks and Recreation department to assess feasibility, and published a version of her speech on the site ‘06880’ to drum up interest in the concept, which she called “Dogport.” Andrew Colabella, a member of the RTM representing District 4, got in touch with Emme shortly after her essay on ‘06880’ went live. “Ever since I was a kid, there have been incidents of dogs running out of Winslow Park,” he tells Westport Lifestyle. He had been working on a dog run concept of his own, and Emme and Andrew teamed up to bring their shared vision to life.  They launched a survey in collaboration with @westportmoms on Instagram to gather input from the community, and heard feedback on what worked (and didn’t work) in neighboring towns. Over the course of nearly six months, the proposal crystallized: two fenced-in areas, one for large dogs and one for small dogs, located in a to-be-determined chunk of the 29-1/2 acre Winslow Park. The runs would be self-policing, like the current park. (Rules & regulations would be enforced by Animal Control, and maintenance, including an annual five-week closure for grass care, would be done by the Parks Department.) Funding to launch the dog runs is being done privately, including by the sale of Dogport merch and donations. At press time, the Dogport concept was still in the planning stage.

While the idea wasn’t without some pushback, Emme stresses that their hopes for Dogport go back to her original vision of having somewhere safe for pups like Bode and Ozzie, who don’t do well in open spaces. “This is for our town,” she says. “There are many people who don’t feel safe taking their dogs to Winslow. We’re trying to help all residents have an option.”

ARTICLE BY DR. JENNIFER WIDER

SPORTS & Mental HEALTH

Perspective from a leading doctor—and

local coach—on supporting student-athletes.

In Westport and surrounding towns, participation in athletic programs at the high schools is way above the national average. Varsity athletes in the public and private schools are in constant pursuit of excellence, whether it’s earning a spot on the starting lineup, getting recruited to college as a scholar athlete, or obtaining local and state recognition. Yet underneath the championship mentality lies a more complicated picture of the mental toll, often carried silently by the athletes.

As a high school tennis and squash coach and a doctor, I have noticed the prevalence of anxiety, depression, and stress-related conditions among athletes, which has steadily increased since I first started coaching. The academic rigor of the award-winning local high schools often adds to the stress, as student-athletes struggle to strike a balance between their classes, sports teams, and socializing with their friends.

“My brother is a recruited athlete,” Maddie*, a rising senior at Staples High School, told me. “So there’s a lot of pressure on me too.” When asked where the pressure was coming from, Maddie replied: “Mostly myself, but my parents too.” Maddie is on a varsity team at Staples, she’s a straight-A student (except for one class), and she often stays up past 1 am to do her homework, even when she has a game the next day. “I’m always exhausted and stressed. That’s my baseline.”

A recent study published in the National Library of Medicine, “Prevalence of Stress Amongst High School Athletes,” cites a staggering 91 percent of high school student-athletes report experiencing some level of stress associated with balancing sports and academics. Fifty-eight percent report experiencing moderate-to-severe stress. Other studies highlight the prevalence of

anxiety, depression, burnout, and other stress-related conditions among high school athletes. Only 10 percent of student-athletes seek professional mental health care.  It isn’t surprising that Maddie is stressed and exhausted, and her feelings are shared by many student-athletes who have tied much of their self-worth to their athletic performance. When time on the field or court changes, or they get injured or struggle, it not only hurts their confidence, it triggers feelings of unworthiness. But perhaps no factor has changed the amount of pressure more than social media. The digitalization of sporting events keeps the athletes on a public stage 24/7, replaying highlights and/or failures. Social media magnifies comparison, creates an omnipresent news cycle, and often serves as a space where losses become compounded by digital commentary.

Early sports specialization, where students focus solely on one sport all year round, adds to the pressure. In previous generations, high school athletes were encouraged to play multiple sports. Now more than ever, it is common to specialize in one sport by the age of 12, train all year, and exclude other sports. Studies show that this trend contributes dramatically to stress and burnout in young athletes.

In Westport and surrounding towns, the drive to support a child’s success is tangible. But the mental health of student athletes is definitely an issue that needs to be placed on the parental radar screen. There are actionable steps parents can take to protect their child’s sense of well-being that start with normalizing conversations about mental health at home and encouraging your child to speak up when they are struggling. Parents who have open and honest conversations with their children often raise

“We take a collaborative and proactive approach to support student-athlete mental health.”

children who will advocate for themselves in times of need. Help your child understand that your love and admiration is unconditional, and not indelibly tied to whether they win or lose. In addition, the aftermath of competition is a time to decompress, not a time for critiques and advice.

We are lucky to live in a town that recognizes some of the challenges. Both Staples High School and Greens Farms Academy (GFA) have put measures in place to address and manage student- athlete stress and anxiety.

“We take a collaborative and proactive approach to support student-athlete mental health,” says VJ Sarullo, the athletic director at Staples High School. “Our athletic department and its staff work closely with school counselors, teachers, and administrators to ensure that student-athletes know support is available and accessible.” Parents, also, should remind their children that this kind of support is available.

“At GFA, we are deeply committed to the holistic wellness of our student-athletes. This upcoming school year, we are introducing a new athletic offering which will focus on movement and mindset, teaching students vital skills like breathwork, visualization, and physical recovery,” says Jennifer Harris, the associate director of athletics at GFA. “We are actively looking for creative ways to build in ‘off’ days, giving our students much-needed ‘found time’ to rest, recharge, and pursue other passions.”

Being part of a sports team is a wonderful opportunity for growth, resilience, and community. Recognizing the pressure and mental challenges that our students face and managing them as parents, coaches, and administrators, we can ensure that our kids are building the skills they need to become better competitors and healthier young people.

*Name has been changed

Sources  Jayanthi, N. A., Post, E. G., Laury, T. C. et al (2019). Health Consequences of Youth Sport Specialization . Journal of Athletic Training.

Dr. Jennifer Wider is a women’s health expert, author of four books, and radio host. She has appeared on The Today Show, CBS News, CNN, and ABC News Nightline. She is a graduate of Princeton University and received her medical degree from the Mount Sinai School of Medicine in New York City. Dr. Wider was a collegiate athlete, and in her spare time, she coaches high school tennis and squash teams in Connecticut.

Morgan Stanley

Portfolio Manager Senior Vice President Financial Advisor

Dogs With Jobs

MEET LOCAL PUPS WHO ARE MORE THAN JUST PETS.

BY SARA GAYNES LEVY

Ella, aka @elladaberner

Age: 5 | Breed: Bernese Mountain Dog | Job: Therapy Dog

Ella’s owner Sarah Greve had always wanted a dog as a child, but her siblings had severe allergies to pet dander. So when she met her now-husband, who had grown up with Bernese Mountain Dogs, they quickly decided the breed would be their first shared pet. They got Ella five years ago, though Sarah didn’t have plans to pursue the therapy dog route at the time. “I have a background in social work, so I learned what a therapy dog was when I was interning at a pediatric ICU,” she says. “But I didn’t know that was something we would do.” But when Sarah’s son Walt, now 4, was diagnosed with autism at 18 months, she began studying the impact Ella had on him more closely. “She was the only thing he would interact with, look at, touch,” she says. “She has been such a rock for him. I thought, ‘I have to get her therapy dog certified to spread this love.’”

After completing the training, Sarah began taking Ella to volunteer, both at the Westport Library’s Reading to Rover program and at Bridgeport Hospital, where they head every Friday. “We go to pediatrics, oncology, and see hospice patients. Because of her size, when she’s standing, her head rests right on the hospital bed. Patients get to look at her sweet face, rub her ears, and smile, even under the worst circumstances.” The work has turned into the ultimate calling, for both Sarah and Ella. “There’s something that dogs do by being silent and giving that unconditional love, especially in a hospital setting,” she says. “Patients don’t have to tell Ella why they’re in the hospital, or why they’re sick. She is such a comfort. It just warms my heart.”

Brutte and Ambo

Ages: 9 | Breed: Belgian Malinois (Brutte) and Yellow Labrador (Ambo) | Job: Police Dogs

Brutte, a patrol dog, and Ambo, an explosives detection dog, are the constant companions of Corporal James “Jimmy” Loomer of the Westport Police Department, who has been working in the K9 Unit at the WPD since 2012.   “They only patrol with me, and when I’m off, they live with me and my family,” Jimmy tells Westport Lifestyle. When Jimmy is on a shift, the dogs tag along, patrolling, but because the WPD is a small department, Brutte and Ambo often get called in when another officer “needs a nose,” even in neighboring towns like Fairfield. “So that could be tracking someone, or finding explosive or drug odors,” Jimmy explains.

Jimmy did a ten-week training course with his dogs to prep them for the realities of the job: responding to only his commands, getting them comfortable in many types of environments, and learning to detect specific narcotics/ explosives odors. “When we first get these dogs, they’re kind of like young boxers,” he says. “They have the genetics. We just have to teach them the techniques.” And once they’re up to speed, they’re an invaluable resource. “There’s no piece of technology that can beat the nose of a dog,” says Jimmy. “And they love to work. For them, it’s a game. Our dogs are play reward dogs, and after [they finish a task], they get either a bite toy or a tug toy. That’s their payment, and that’s what they love best.” (It’s worth noting that community donations cover actual payment for the WPD’s police dogs’ food and vet care; to learn more or donate you can reach out to Cpl. Loomer directly at jloomer@westportct.gov, or make a check payable to “Westport Police K-9 Unit.”) “Dogs are man’s best friend, and there’s an awesome loyalty that comes with them,” says Jimmy. “It’s an honor to be able to be a handler.”

Oakley

Age: 9 | Breed: Australian Shepherd/Great Pyrenees mixed breed | Job: Therapy Dog

When Ruth Ayles was looking to adopt a rescue dog eight years ago, she was working for a pet-friendly company, and hoped to find a dog with a temperament that would be compatible with an office environment. Adopted when he was 88 pounds and a year old, Oakley was perfect from minute one. “He got along with all the other dogs, people, and kids,” Ruth says. After seeing how so many were drawn towards him, including toddlers, “I thought: I wonder if he would make a good therapy dog.” So Ruth and Oakley registered as a therapy dog team with Pet Partners (for more on this, see page 51), and he handled everything flawlessly, including tests of obedience, busy situations (at times involving medical equipment), loud noises, and lots of people  interacting with him at once. He demonstrated an ease and willingness to engage in the therapy work. As

part of the team, Ruth advocates for Oakley during volunteer visits to ensure his comfort and well-being, guides interactions, and makes sure the visit goes safely and smoothly for everyone.  Once Oakley officially became a therapy dog, they began volunteering at The Westport Library’s Reading to Rover program, doing wellness programs and crisis therapy at schools including Staples High School and New Canaan High School, and visiting nursing homes. “It’s a really wonderful feeling to be volunteering, giving back to the community, and doing it with your dog,” says Ruth. “I see the connection that Oakley brings to the people we visit, and it’s so rewarding. Many people, particularly elderly, will say ‘I used to have a dog,’ and they really miss that connection with an animal.” It’s the kind of job anyone—human or canine—can’t help but enjoy.

Dogtor Bill

Age: 14 (approx.) | Breed: Beagle | Job: Pediatrician’s Assistant

Dr. Nikki Gorman adopted Bill nine years ago—she was surfing Petfinder and was struck by how much Bill reminded her of her childhood dog Barney. After he came home and she studied his calm, cuddly personality, she started bringing him along to Village Pediatrics, where she has worked for 17 years as a pediatrician. “He’s a very mellow soul, and most of the time he’s sleeping under my desk,” Dr. Nikki says. “But he seems to have a sense of when somebody

needs him. He knows the patients who love him, and it’s like he smells them–he just noses his way into the room. It’s so cute and they’re always so tickled to see him.” While Bill may not know he’s considered a member of the staff at Village, he loves heading to work. “I actually have another dog who doesn’t come to the office, and when we go on their morning walk, Bill goes to the car and just stops,” says Dr. Nikki. “He’s always happy to go.” And once he’s there, he knows just what to do. “I’ve noticed that if there is anxiety in the room—whether from a parent or a patient—he will come in. He brings a sense of peace.” Bill has even helped some patients who might have a fear of dogs—because he’s older, he can’t jump, and he was adopted with a condition known as “crate teeth,” where he has no front teeth due to being left in a crate for too long and trying to chew his way out, so he physically cannot bite. “He’s never growled in his life. He’s such a gentleman!” Dr. Nikki says. Having a “dogtor” on the team has become one of the best things about Village. “Kids are excited about the prizes, and they love the lollipops, and we like to think they like us,” says Dr. Nikki with a laugh. “But when they see Bill, they just light up.”

Age: 6 | Breed: Mini Goldendoodle | Job: Therapy Dog

Zane is actually Jen Krasnow’s second therapy dog—her first, a 15-year-old medium Goldendoodle named Kako, retired in April after a nine-year career. Therapy dog handling first called to Jen nearly 15 years ago, after her father’s spirits were immesurably lifted from a visit with a therapy German Shepherd while hospitalized. The idea stayed in the back of her mind for years, until, in 2017, she finally decided to sign Kako up for a class at Dog Gone Smart in Norwalk with Pet Partners, a therapy-dog registration organization, to become a therapy-dog handler. “I can’t even tell you how excited I was after that first class,” she says. Over two months, Jen (who was later joined by her daughter) completed the class, and Jen then went through the online exam and in-person evaluation required for therapy dog registration through Pet Partners. Kako soon became a regular at Cambridge Health and Rehabilitation Center, the Westport Library’s Read to Rover program,

and Mosaic Senior Living. Just a few years later, during the pandemic, Jen became a licensed evaluator for Pet Partners, helping to create more therapy dog/handler teams and to become a part of the organization that had given her and Kako so much. And then, after Kako’s retirement earlier this year, she got Zane registered, too, and they’ve continued the valuable work she started nearly a decade ago. Zane and Jen now visit new volunteer spots, including St. Vincent’s Behavioral Health and Staples High School. “When you come into a room with an animal that’s calm and gentle, the whole atmosphere changes,” says Jen. She loves how therapy dogs form genuine connections, wordlessly and instantly, with whomever they’re visiting. “The dog is there to see you , and spend time with you. To have a dog that leans into you, or is looking at you, it’s such a positive sensory experience. People are so grateful and appreciative.”

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CULINARY• EVENTS • LIFESTYLE

THE WESTPORT LIFESTYLE GUIDE TO SAVING FOR COLLEGE

LOCAL FINANCIAL PLANNERS HELP EXPLAIN THE PROCESS.

For many parents, the largest single expense they will have for their children is college. The cost is skyrocketing: for the 2026-2027 school year, in-state tuition plus expenses at the University of Connecticut is $36,758, while the total at nearby private school Yale is an eye-popping $94,100. Luckily, while costs seem out of control, saving for higher education doesn’t have to be complicated. Westport Lifestyle spoke to trusted experts for their top saving-for-college tips heading into this school year.

529 PLANS FOR COLLEGE SAVINGS

Financial professionals often recommend considering a 529 account for college savings. “I would suggest opening a 529 for each child when your children are young, and beginning to save small amounts on a regular basis,” says Michael Wein, Financial Advisor at The Wein Group, Morgan Stanley Wealth Management. If you’re not familiar, 529s are investment accounts designed to provide tax advantages for families saving for educational costs. “They grow tax-free and, when you withdraw funds for qualified educational purposes, they’re tax-free withdrawals as well,” explains Koy Price, Associate Financial Representative at Saugatuck Financial. (And “qualified educational purposes” includes not just tuition but room, board, books, and meal plans, says Koy.) “If a child is planning on going to college and that’s something the family wants to fund, a 529 can offer serious tax advantages.”

BALANCE YOUR GOALS

While the exact amount you save—and how often you make contributions— is an individual choice, “in simplified terms, we recommend early and often,” says Spencer Avalos, Managing Partner at Darwin Wealth Management. But that doesn’t mean neglecting other long-term savings goals, like planning for retirement. “Having a plan that takes care of both—that makes sure your retirement is strong as well as creating opportunities for your children—is huge,” says Koy. “Retirement planning is an important consideration alongside education savings.” Spencer agrees: “Priority-wise, your most expensive goal for most people is retirement—it’s like putting your own oxygen mask on first,” he says.

The structure Spencer generally recommends is figuring out how much you need in cash savings and how much should be going towards retirement. “Anything outside of that needs to be working for some goal of yours,” Spencer says—including college savings, of course. “By establishing those goals early, you can reverse engineer [your contributions] from there.”

EMBRACE THE FLEXIBILITY

“The plans are more flexible than you think,” says Michael. For example, while he recommends having a 529 account for each child, any unused funds can be rolled over between children, used for graduate school, or even passed on to the next generation. Additionally, explains Koy, in 2026, up to $35,000 can be rolled over into a Roth IRA for the child, to start their retirement savings journey. (Withdrawals not used toward education or the Roth IRA allotment are subject to ordinary income tax on the gains, as well as a 10 percent penalty on the gain.) So while you don’t want to deliberately, massively overfund a 529, there are plenty of options if you do find yourself with excess savings in the account—which is, of course, much better than the alternative of not having enough!

IT’S NEVER TOO LATE

There are benefits to using an education savings plan, no matter how old your children are.  “Maybe what goes into it changes because you’ll be using it sooner than, say, the parent of a one or two-year-old who can take on a little more risk, but it’s never truly too late,” says Spencer. Another thing that can help if you’re behind on the savings game: “529s allow you to, basically, fund up to five years of the gifting limit in a single year,” says Michael, and that’s per person, so a married couple could conceivably add up to $190,000 at once, for a jump-start.  No matter what, “when it comes to having these dollars invested,” says Koy, “anything is better than nothing. Tax deductibility [in Connecticut] and tax-free growth, even if the child is older, may be a good strategy.”

DISCLOSURE:

This publication is provided for informational purposes only and is not intended as financial, legal or tax advice. Please see your Financial Representative for specific recommendations to meet your personal needs and objectives. Financial Representatives do not render tax advice. Consult with a tax professional for tax advice that is specific to your situation. All investments carry some level of risk, including loss of principal invested. No investment strategy can assure a profit and does not protect against loss in declining markets.

Members of Saugatuck Financial use Saugatuck Financial as a marketing name for doing business as representatives of Northwestern Mutual. Saugatuck Financial is not a registered investment adviser, broker-dealer, insurance agency or federal savings bank. To view detailed disclosures regarding individual representatives, view their information at https://www. saugatuck-financial.com/.

Northwestern Mutual is the marketing name for The Northwestern Mutual Life Insurance Company (NM) and its subsidiaries including Northwestern Mutual Investment Services, LLC (NMIS) (Investment Brokerage Services), registered investment adviser, broker-dealer, and member of FINRA and SIPC, in Milwaukee, WI.

The 529 Plan Program Disclosure contains more information on investment options, risk factors, fees and expenses, and potential tax consequences. Investors can obtain a 529 Plan Program Disclosure from their Financial Advisor and should read it carefully before investing. Investors should also consider whether tax or other benefits are only available for investments in your home state 529-college savings plan. Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors or Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for legal matters. Morgan Stanley Smith Barney LLC. Member SIPC.

Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors or Private Wealth Advisors do not provide tax or legal advice. Individuals should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trusts, estate planning, charitable giving, philanthropic planning or other legal matters.

Your Next Chapter Depends on Your Next Move

High Conflict, High Net Worth, and Highly Complex Divorces

ATTORNEYS AT LAW

JACQUELYN CONLON | BONNIE AMENDOLA

281 Pequot Avenue, Southport, Connecticut 203-803-2943

Westporter Missy Greenberg makes cherished pets into works of art.

PORTRAITS FOR PETS

ARTICLE BY SARA GAYNES LEVY | ARTWORK BY MISSY GREENBERG

“Anyone who knows me knows I love animals,” says Missy Greenberg, a Westport-based wife, mom of two boys, dog mom to a one-year-old pup named Penny, lifelong vegetarian, and the artist behind custom pet portrait studio, Painting Paws by Missy. “I could really paint anything: scenic work, or portraits. But I decided to launch a pet portrait business because I have an innate love for animals.”

There is more to Missy’s story than that, of course. After a decade-long career in public relations and the birth of her second son, Missy was in search of something more fulfilling. So, in the middle of the pandemic, with a four-month-old baby and almost three-year-old at home, Missy enrolled at Hunter College in New York City, earning a second Major in Fine Arts, and then went on to earn a Master’s degree in Art Education from Fairleigh Dickinson University. “It was my favorite schooling experience I’d ever had, because my heart was in it,” she says.

Missy and her family moved to Westport in 2023, and she launched “Painting Paws by Missy” shortly after, in 2024, as a way to combine her favorite things: animals and artwork. “I’ve had all sorts of animals throughout my life: cats, birds, fish, hamsters,

and now a dog. And I’ve loved making art for as long as I can remember. I feel like it’s a dream that I found a way to marry these lifelong passions,” she says. She primarily receives commissions through her Instagram, where the client will then send a “character-forward photograph” of the animal subject for Missy to work off of. (For local pets, Missy can also come and photograph them herself, at no extra charge. “I just love to be around animals, so any chance I get to meet the animal that I’m painting, all the better!” she says.) Together with the client, they’ll pick a background color or setting, and the custom portrait is usually ready in about a month. She’s an expert at details, like eyes, that allow the animal’s personality to shine through. “Sometimes, the animal has since passed, so the artwork becomes very special because I’m making a keepsake of a pet who is no longer with us.” One of her favorite pieces was a painting depicting all seven dogs a 75-yearold woman had owned in her lifetime, all along her favorite beach in Charleston, SC, given as a birthday gift. “I get chills talking about it!” Missy says. Last year, she donated a portrait to the family of a dog that was lost on the Merritt. She’s also donated custom works to local organizations like Neighborhood Studios

(an art nonprofit out of Bridgeport), the Hearts in Harmony Foundation, Long Lots School, and The Learning Community Day School. She’s even done a few inanimate furry friends: paintings of beloved childhood stuffies, it turns out, make great bedroom decor.

Since starting two years ago, Missy estimates she’s done about 40 paintings. “My children are so proud to tell their friends that their mom is a real artist,” she says. “Every time they beam, I have to pinch myself. This business is a joy of my life,” says Missy. “I really think this is what I was destined to do.”

Missy’s acrylic paintings start at around $400 (for an 8"x10”). For more information or to book a commission, contact PaintingPawsbyMissy@gmail.com or follow @PaintingPaws_byMissy on Instagram.

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Summer's Last Hurrah

Five easy escapes to savor the final days of the season.

ARTICLE BY ELIZABETH GINNS BRITTEN

Years ago, someone—pretty sure it was my brother—said to me, “August is like one long Sunday night.” Every year around this time, I find myself thinking about that phrase. The sun starts setting earlier. The first day of school appears on the calendar. Fall sports practices and carpools creep into the schedule. As Labor Day draws near, the carefree feeling of summer begins to slip away.

As the mother of two teenagers, I’ve learned that summer doesn’t necessarily get less magical as children get older. It just gets shorter. Which is why I’m a big believer in squeezing in one last adventure before the school year begins.

The good news is that living in Fairfield County puts us within driving distance of some incredible destinations. Whether you have a free day, a spare night, or an open weekend, these easy getaways offer one final chance to make a summer memory before backpacks, lunchboxes, and alarm clocks return.

BLOCK ISLAND: THE ISLAND ESCAPE

Even the journey to Block Island feels like an adventure. Ferries depart regularly from Point Judith, Rhode Island, and in less than an hour, the mainland begins to disappear.

The island is compact enough to explore on two wheels, so rent bikes at the ferry terminal—half the fun is discovering what lies around the next bend in the road. Spend the morning at Crescent Beach, then make your way to the dramatic Mohegan Bluffs, where a steep staircase leads down to one of the most spectacular stretches of shoreline in New England. Nearby, the Southeast Lighthouse sits atop the cliffs, offering sweeping views of the Atlantic.

Have a lobster roll lunch, overlooking the harbor. After, wander through Old Harbor's collection of shops and galleries, or find a quiet patch of beach and settle in. The beauty of Block Island is that it doesn’t require a packed itinerary. A bike ride, a beach, an ice cream cone, and nowhere in particular to be is the itinerary.

NEWPORT: A WEEKEND IN THE GILDED AGE

Newport has beaches, harbor cruises and waterfront restaurants—and I do recommend sampling all of that!-— but the town’s enduring appeal lies in the way it blends history, glamour, and classic New England charm. For anyone who has recently become obsessed with HBO’s The Gilded Age, Newport offers the opportunity to step inside the world of the Vanderbilts, Astors, and more of America’s wealthiest families.

Start with The Breakers, the Vanderbilt family’s spectacular 70-room summer “cottage,” where marble staircases, gilded ceilings, and ocean views reveal the staggering wealth of the era. Nearby Marble House, built by William K. Vanderbilt as a birthday gift for his wife Alva, is equally fascinating and every bit as extravagant (this one is actually my personal favorite; the gardens in particular! Think: Hydrangea heaven).

“As the mother of two teenagers, I’ve learned that summer doesn’t necessarily get less magical as children get older. It just gets shorter. Which is why I’m a big believer in squeezing in one last adventure before the school year begins.” “

After touring the mansions, head to the famed Cliff Walk, where crashing Atlantic waves sit on one side, and Newport’s grand estates rise on the other. Even a short stretch of the walk delivers some of the most iconic views in New England.

For lunch, grab a table at The Black Pearl on Bannister’s Wharf for its clam chowder and harbor views. Spend the afternoon browsing the shops along Thames Street and Bowen’s Wharf before ending the day aboard a sunset sail through Newport Harbor. Watching the sun dip below the horizon as sailboats glide across the water is one of those experiences that never gets old.

THE BERKSHIRES: SUMMER’S LAST DEEP BREATH

The Berkshires’ rolling hills, charming towns, lakes, hiking trails, and outdoor concerts create an atmosphere that practically forces you to relax. Families can spend the morning paddleboarding on Stockbridge Bowl, hiking Monument Mountain, or exploring the grounds at The Mount, author Edith Wharton’s former estate.

In Great Barrington, independent bookstores, cafés, and boutiques invite leisurely browsing. Nearby farm stands overflow with late-summer produce. As evening approaches, many families spread out a blanket on the lawn at Tanglewood, home of the Boston Symphony Orchestra's summer season. Even reluctant teenagers tend to appreciate a picnic dinner as the sun sets behind the mountains and music fills the air.

By late August, the crowds thin and the evenings grow slightly cooler, making it an ideal place to savor summer’s final weeks.

LAKE GEORGE: CLASSIC SUMMER NOSTALGIA

There is an old-fashioned quality to a weekend in Lake George that feels refreshingly simple. Kids make friends at the beach. Families enjoy hours on the water, swimming, boating, and tubing. Rent a pontoon boat and spend an afternoon exploring the lake’s coves and islands. Take a cruise aboard one of the historic Lake George steamboats. Wander the village, challenge the kids to a round of mini golf, and finish the evening with an ice cream cone while strolling along the waterfront.

Surrounded by the Adirondack Mountains, Lake George offers just enough adventure while remaining wonderfully accessible. If your goal is to squeeze every last drop out of summer before school begins, Lake George is hard to beat.

THE NORTH FORK: A GETAWAY ON THE WATER

Fairfield County families can board the Port Jefferson Ferry in Bridgeport and enjoy a scenic and traffic-free crossing of Long Island Sound, and from Port Jeff, it’s about an hour's drive east to the North Fork. There, a very different version of Long Island awaits, full of farm stands, fishing boats, and quiet beaches.

Spend an afternoon exploring Greenport, one of the region's most charming waterfront villages. Browse local shops, enjoy homemade ice cream from Aldo’s, or watch boats coming and going from the harbor. Families can spend the day at Orient Beach State Park, known for its calm waters, easy trails, and beautiful views.

Late August is prime farm-stand season, and roadside markets overflow with peaches, sweet corn, tomatoes, and fresh flowers.

The North Fork lacks the see-and-be-seen atmosphere of the Hamptons, and that may be the best part.

ONE MORE THING

Years from now, our children probably won’t remember whether the trip lasted one night or four. They won’t remember how much we spent or whether every detail went according to plan. What they’ll remember is racing down a hill on Block Island, standing inside a Vanderbilt mansion, jumping off a dock into a lake, watching sailboats on Newport Harbor, or eating ice cream on a ferry ride home as the sun sets over Long Island Sound.

August may feel like one long Sunday night, but remember: there’s still time before Monday morning arrives.

Another

Spanning

TREY & KATIE KENNEDY

ON MARRIAGE, KIDS, AND THE COMEDY OF REAL LIFE

Trey Kennedy makes a living finding comedy in regular life. Marriage. Toddlers. Yoga pants. The Thursday-night scramble between school dropoffs, soccer practice, and whatever has to be done by morning. Twelve years in, it shows: millions of followers across every platform, three stand-up specials, a sold-out Relatable Tour, and a style of humor fans send each other captioned, “Are you watching me?” He delivers the kind of comedy that travels because everyone’s living some version of it.

Katie, his wife of six years, is a former biomedical engineer who also built a modeling career. She’s now raising their kids and co-hosting Correct Opinions alongside Trey — the show where the two of them swap takes on marriage, parenting, and whatever came up that week.

Trey has been at this longer than people realize. An Edmond, Oklahoma kid who grew up playing basketball described himself as a “shy kid who never thought he’d be an entertainer.” He started making videos while attending Oklahoma State University. After building millions of followers on Vine before the platform shut down, he gave himself six months on Instagram and Facebook to see whether he could rebuild from zero. He did. Stand-up soon followed. His first special, Are You For Real?, streams on YouTube; the second, Grow Up, on Amazon Prime; the third, built around the Relatable Tour, wrapped earlier this year. “I’ve been trying to be funny every week for like twelve years now,” he says. A slow climb, made one bit at a time.

ARTICLE BY KALI KASPRZYK

“I’ve been trying to be funny every week for like twelve years now.”

Most of what Trey writes lately starts in his own kitchen. Thomas is three and a half, and he is, in his father’s words, “a movie.” He narrates his own life from the moment his eyes open and mispronounces words in ways his parents now repeat to each other because no one else would believe them. His younger sister, Eva, is what Katie calls “the calm one.” With a third now in the mix, the Kennedys are officially outnumbered.

After six years of marriage, Trey and Katie have learned that the partnership runs best when it gets its own time on the calendar. So once a week, they leave the kids with a sitter and go out for coffee. “You need a system,” Katie says. “It’s about taking time to look each other in the eye. Not the kids. Not the cameras. Just each other.”

The same instinct shapes the work. Most of Trey’s trial and error happens onstage or on Instagram, but the first read is always Katie’s. “There’s only been one time ever I’ve had to be like, ‘you’re not doing that,’” she says. The rest of the time, she just laughs first.

FEATURING TREY & KATIE KENNEDY

Trey and Katie talk about marriage, parenting, and the moments that don’t make the Instagram feed.

Watch or listen to the full conversation wherever you get your podcasts.

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AUGUST 2026

A SELECTION OF UPCOMING LOCAL EVENTS

AUGUST 1ST

Agatha Christie's The Murder of Roger Ackroyd

Westport Country Playhouse, 25 Powers Ct. | 3:00 PM

The final two performances of the 2025/2026 season at the Westport Country Playhouse are on August 1st at 3:00 and 8:00 p.m. Catch this twisty murder mystery, adapted for the stage by the Playhouse's own Artistic Director Mark Shanahan, before it's gone. Tickets, $50, at westportplayhouse.org

AUGUST 1ST

Nic & Desi: Broadway to Hollywood

Music Theatre of Connecticut, 509 Westport Ave., Norwalk | 8:00 PM

Alumni performers Nicolas Dromard and Desiree Dava, who have appeared on Broadway and national tours of  Wicked, Jersey Boys, Mary Poppins, West Side Story, and  Peter Pan,  will perform hits from Broadway, the American Songbook, and the golden age of Hollywood. Tickets, $55, at  musictheatreofct.com

AUGUST 7TH

Devon Gilfillian: Time Will Tell Tour

The Levitt Pavilion, 40 Jesup Rd. 7:30 PM

Devon Gilfillian's music combines rock, funk, and country on the album Time Will Tell, produced by Neal H. Pogue (who has also worked with Tyler the Creator and OutKast). Tickets: free. For more information, visit  levittpavilion.com

AUGUST 8TH

Katona & Kittredge: Key Changes

Music Theatre of Connecticut, 509 Westport Ave., Norwalk | 8:00 PM

Ann Kittredge and Raissa Katona Bennett—two award-winning NYC cabaret artists with credits spanning Broadway, Off-Broadway, and as true New York performers, even Law & Order: SVU—join forces for an unforgettable evening of song. Tickets, $55, at  musictheatreofct.com

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Sun’s Out. Studs Out.

The Levitt Pavilion, 40 Jesup Rd.

13-time Grammy-award winner and member of the Rock & Roll Hall of Fame Bonnie Raitt headlines the Levitt Pavilion's annual gala. All tickets include chairs. Tickets, from $365 for concert only, and $505 for the cocktail party at Massi Co. and Walrus Alley + levittpavilion.com

The Levitt Pavilion, 40 Jesup Rd.

Touring for their new album, Get It Honest, the New Orleans-born The Revivalists appear again at the Levitt Pavilion. They have "earned a national following with their fusion of indie rock, soul, and folk." Chairs provided at this performance. Tickets, from

AUGUST 15TH

The Moonrise Cartel

Lachat Town Farm, 1 Ladder Hill Rd. South, Weston | 6:00 PM

The Moonrise Cartel is "folk rock from Black Rock" and appears as part of the wildly popular Music in the Meadow series at Lachat Town Farm. Also appearing: Brian Dolzani as "The Loner," performing the music of Neil Young. Tickets, from $39, at eventbrite.com

AUGUST 15TH

Cracks And All by Randye Kaye

Music Theater of Connecticut, 509 Westport Ave., Norwalk | 8:00 PM

Randye Kaye’s one-woman show got its start in a storytelling and comedy class at MTC, taught by Lisa Lampanelli. Randye, a voice actor, is best known as news anchor/local host of All Things Considered for WSHU Public Radio, and is the host of its new podcast Good At Heart. Tickets, $45, at musictheatreofct.com

AUGUST 15TH

Jordan Jensen

District Music Hall, 71 Wall St., Norwalk | 7:00 PM

Stand-up comedian Jordan Jensen, best known for her Netflix special  Take Me With You, performs at the District Music Hall in downtown Norwalk. Tickets, from $38.52, at  districtmusichall.com

CONTINUED

AUGUST 18TH

Comedy Night

The Levitt Pavilion, 40 Jesup Rd. | 7:00 PM

The Levitt continues their summer of free entertainment with a night of stand-up comedy under the stars. For more information, visit  levittpavilion.com

AUGUST 23RD

Andy Frasco

& The U.N., with Kitchen Dwellers and Magoo

The Levitt Pavilion, 40 Jesup Rd. 5:00 PM

Andy Frasco & The U.N. blend "funk, jazz, surf rock, blues, swing, gospel, reggae, exotica, and more with horn-blasted positivity and soulful power." They'll appear with progressive roots band Kitchen Dwellers and progressive bluegrass quartet Magoo. Tickets, from $61.25, at  levittpavilion.com

AUGUST 24TH

Charlie Hall's Get Up With It: A Miles Davis Centennial Celebration

The Levitt Pavilion, 40 Jesup Rd. 7:00 PM

As part of their America250 series and in honor of Miles Davis’ 100th birthday, GET UP WITH IT, the longstanding project of The War On Drugs drummer and Wilton native Charlie Hall, will take the Levitt Pavilion stage. Tickets, from $25, at levittpavilion.com

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ARTICLE BY SARA GAYNES LEVY

As the mom of three young kids (plus one elderly dog), the August Family, Kids + Pets issue is one of my favorites to work on. There are so many amazing kid-friendly places in Westport, and it feels like another opens every day. But for the past three years, my kids have counted the Westport location of membership-based indoor play/funland The Wonder as one of their most loved. When my oldest was 18 months old, we visited their original location in TriBeCa, and were charmed by the friendly staff and multitude of activities. When one opened in Westport—the founder and CEO, Sarah Robinson, moved to town during the pandemic—we were quick to join. Having an indoor playspace for rainy, unbearably hot, or frigid-cold days is just one of the perks of membership: there are also inventive classes, an immersive black box space where staffers lead kids on teddy bear picnics and bubble discos, guided crafts, camps during school breaks, and a family movie night every Friday. Sarah herself is a mom of four, and she brings a playful spirit plus a mother’s intuition about what kids actually like to The Wonder’s colorful programming. (On the strength of her vision, a third location is opening in late 2026 on New York’s Upper West Side. The original TriBeCa location has since moved to Brookfield Place.) So to my fellow parents, as you gear up for the 2026-2027 school year, remember: the next time your kids are bouncing off the walls at home, crying “I’m bored?” You know where to go.

The Wonder is located at 1200 Post Road E., for more information on membership visit thewonder.fun