It is my great joy to present Westport Lifestyle's annual Women of Westport list: a roundup of some of the most inspiring, influential, creative, community-driven women in Westport, Weston, and Wilton. These 12 women represent the true range of talent we have here in our community, and I hope you have as much fun—and learn as much!—getting to know them as I did. Congratulations to these impressive women. I can't wait to see who joins their ranks in 2027! -Sara Gaynes Levy, editor
Melissa Conner
partner at Jennifer Bett Communications, co-founder of After Hours Capital, brand ambassador, The WIE Suite
A connector at heart: “In college, I landed an internship at a wonderful boutique PR agency, and it completely changed my trajectory. That experience is where I fell in love with communications. As my career has evolved, what continues to draw me in is storytelling and relationships. At my core, I believe that success expands when it’s shared. Throughout my career, so many women opened doors for me, made meaningful introductions, or offered guidance at pivotal moments, and that generosity left a lasting impression. Connecting people feels very natural to me because I’m endlessly curious about what others are building and how they might support one another. Community has always been a throughline in my personal and professional life.”
Championing Fairfield County: “I was born and raised in Connecticut, but I never imagined I’d move back. The pandemic brought me home, and it’s been the best surprise. Weston is such a special place. After moving back, I realized there were so many accomplished women here, yet fewer intentional spaces for meaningful connection. It felt like the perfect moment to build a community that reflects that. Bringing The WIE Suite to Connecticut was about creating the kind of network I wished existed when I first returned—one that fosters collaboration over competition and cultivates real relationships, not just networking moments.”
Support from all sides: “Public relations is often fast-paced and behind the scenes, but stepping back, you realize you’ve helped shape narratives and support people during pivotal chapters of their journeys. That’s incredibly fulfilling. When women show up for each other, incredible things happen.”
Ashley Holt
cake artist, culinary producer, and creative director of Sugar Monster
From model to cake artist: “Modeling taught me independence and gave me a front-row seat to creativity at a high level. But it also came with challenges, and while looking for an escape, I discovered I felt most grounded when I was making something with my hands. Baking started as therapy. It was creative, quiet, tactile, and satisfying in a way fashion never quite was. I expanded to small cake orders, learned new techniques, and challenged myself to build experience. The turning point was competing on Cake Boss: Next Great Baker. Winning that show at 25 opened my eyes to the world of food media.
Being able to build a creative career while being present for my family and the life my fiancé and I are building together is, to me, the greatest marker of success.”
Giving back: “This is home. My daughter is growing up here. These are the beaches we go to, the sidewalks we walk, the playground she’ll always remember. Being part of something like the Compo Beach build just felt right. Getting to show up and work with power tools alongside strangers who quickly became friends? Sign me up.”
Creativity and connection: “My favorite thing about my career is that I get to build, experiment, pivot, and reinvent. I love the freedom that comes with carving out my own path. And there are so many women here building businesses and raising families, including many of my friends. Seeing everyone cheering each other on while continuing to do cool things and prioritizing family creates such a motivating energy.”
Christine Horelick
licensed massage therapist and certified lymphedema therapist
Empathetic hands: “About eight years ago, I started focusing on post-surgical recovery, mainly women recovering from breast cancer and reconstructive procedures. The more I worked in this space, the more it felt like where I truly belonged. [Christine’s mother battled both non-Hodgkin’s lymphoma and, later, breast cancer.] After years of developing emotional resilience and a deep capacity for empathy, supporting oncology patients through lymphatic therapy felt both natural and meaningful.”
More than massage: “I feel incredibly fortunate to have found a profession that brings me so much fulfillment and joy. I work with women from the time they are diagnosed with cancer, through reconstructive and plastic surgery, helping to educate and prepare them. Our sessions are similar to physical therapy, but relaxing. It’s long-term maintenance, but it feels luxurious. I have the privilege of being part of their care team, supporting them in a meaningful way and helping improve their quality of life while they focus on fighting the most difficult battle.”
Building something bigger: “I am the daughter of a small business owner and I believe my work ethic was ingrained in by my parents. I want my children to see that what I do isn’t just massage, It’s about treating people with dignity, and caring for others when they’re vulnerable. Success isn’t just measured by what you have, but by the lives you touch along the way.”
Heather Frimmer, M.D.
board-certified breast radiologist and award-winning novelist
Where science meets art: “When I took a radiology elective in medical school, I knew I’d found my perfect fit. I loved using imaging to solve puzzles, and I appreciated the clinical role breast imagers play in explaining test results. [In 2014], after being in practice for nearly 10 years, I was craving a pursuit that would challenge me to think in different ways. Always an avid reader, I had dabbled with creative writing in the past, so I decided to take an introductory writing class [at the Westport Writers’ Workshop] on a whim. On the last day of class, my instructor strongly suggested I write a novel. I took her up on the challenge.”
Finding community: “By far the most rewarding thing about my second career as an author is the friendships I have made along the way. Be it fellow authors, booksellers, librarians, journalists or Bookstagrammers, the people I have met in the writing community have added wonderful depth, dimension, and meaning to my life. If I hadn’t taken the chance to write a novel, I never would have crossed paths with any of them.”
And nurturing the next gen of writers: “After being a student at the Westport Writers’ Workshop for more than a decade, I joined the board—without the workshop, I would have been writing blind and I never would have had the courage to put my work out into the world. My focus has been to strengthen the workshop community by offering readings and other social events and open writing hours to encourage writers to connect with each other, share their experiences, and write together.”
Robin Jaffee Frank, PhD
Executive Director of the Museum of Contemporary Art, CT (MoCA\CT)
A champion of local arts: “Over the last year, while serving on the Visual Arts Advisory Committee, I didn’t just learn about this institution—I developed a profound belief in its potential. MoCA\CT offers captivating visual art exhibitions, world-class musical performances, and arts education for people of all ages and abilities. We expand minds and hearts.”
Leading a new vision: “Every day, I’m inspired by the talent and commitment of my new colleagues, the support of our Board, the dedication of our volunteers, and the generosity of our members and sponsors. Our mission is clear: we will elevate our curatorial and musical rigor; stabilize and grow our revenue and membership; and deepen our roots in the community. The arts are the social infrastructure of Westport. MoCA\CT will continue to be a place where our community comes together to be inspired.”
Stronger together: “I spent most of my career as a curator of American paintings and sculpture at the Yale University Art Gallery and as chief curator at the Wadsworth Atheneum Museum of Art. It’s a joy to be working in the town I call home, and to have the opportunity to leverage my professional experience to contribute to the arts in my own community. My philosophy is simple: we are stronger when we are collaborative. MoCA\CT is a central cultural partner in Fairfield County and the tri-state area, and we’re strengthening ties with the region’s leading museums. While our institutions vary in scope, our challenges are identical—rising costs and a shifting donor landscape. By aligning our advocacy, we turn individual voices into a cultural chorus.”
Elizabeth Crossfield
licensed marriage and family therapist at Greenwich Psychology Group
Westport on a whim: “We left New York City after my oldest daughter was born. We settled in Westport despite not knowing anyone here. The decision was based solely on the feeling we got when we drove through town once. Connecticut is beautiful and of course we loved being on the water but what was most important to me was having a downtown to walk to. It felt like a good way to transition from city life. At the time, there was a Barneys on Main Street and as embarrassing as this is to admit, that definitely helped sway me! Now, I love the natural beauty, old homes, the dog parks, the restaurants, the cool shops, and the arts community. I have great friends here and my kids still tell me how lucky they feel to have grown up in this town.”
Reinvention at 40: “I am a licensed marriage and family therapist at Greenwich Psychology Group. My first career was in fashion, and I loved it. When I turned forty, I asked myself the question: ‘if I could have had another career what else would I have done?’ The answer was working in psychology, so I gave myself graduate school for my 40th birthday and have been practicing ever since.”
Family first: “I was raised to have a strong family connection. I am someone who needs purpose to feel happy and fulfilled. My work and my relationships are where I put my energy. We are constantly learning from each other, and laugh a lot.”
Rachel Katz Frank, PA-C
owner, Chem Chronos Medical Aesthetics
The art of aging well: “I’ve always considered myself an artist. Drawing and painting have long been passions of mine, and I realized aesthetic medicine beautifully blends my interests in art, science, and procedural work. Starting Chem Chronos allowed me to combine my medical training as a surgical physician assistant, procedural expertise, and artistic perspective to help patients achieve natural, balanced results.”
Finding your best self: “One question I almost always ask is, ‘What is your favorite feature?’ Starting there shifts the focus away from imperfections and toward what makes someone beautiful. My philosophy is always to enhance, not change. The best results are when someone looks refreshed and confident without it being obvious why. I’m also very honest with patients. Sometimes the most important part of a consultation is reassuring someone that they don’t need as much as they think they do.”
Support system: “My husband’s unwavering support gave me the confidence to start my own business. I want my three sons to see their mother as intelligent, hardworking, and capable. At the same time, building my own practice—here, in the town where we live—allows me the flexibility to be present for them when it matters most. I genuinely love what I do.”
Amanda Castellano
Vice President, Investments at Moors & Cabot Investments; board member of the Women's Business Development Council, Fairfield County's Community Foundation, Homes with Hope, and Western Connecticut State University
Fitness to finance: “Sports and fitness have had a great impact on my life. Successful athletes learn the importance of self-discipline, teamwork and community early on. As a personal trainer and, later, company founder, I had the opportunity to hone these skills in order to better communicate with my clients. These same skills are the cornerstone for how I guide my clients today. Understanding not just their financial lives, but also what they envision for themselves and their families over generations.”
A lifelong giver: “I have fond memories of taking part in service projects as a Girl Scout and volunteering alongside my church’s youth group. I saw how giving even a small amount of time can make a difference. From then on, I’ve strived to pay it forward. Westport is a special place because it’s made up of individuals who believe in contributing to the rich fabric of our town. Whether it’s preserving our artistic roots, supporting newly arrived families, or encouraging educational opportunities, Westport is proof of what a thriving community can be when we support our neighbors.”
And mentor: “From experience, everything’s harder when you feel as if you’re the only one doing it. As a female founder, woman in sports, and now in finance, I’ve cherished the mentors I’ve had along the way. That’s why I’m passionate about encouraging and giving visibility to founders who are often underrepresented. If I can help another woman navigate the hurdles that come with scaling a successful venture, why wouldn’t I? As a mentor, I am seeing firsthand the creativity, fearlessness, and unique perspectives that the next generation of leaders brings.”
Jes Parker
founder, Take2Trail
Becoming an ultrarunner: “After having kids, running was the one thing I could get done with whatever time I had. I began to explore obstacle course races and found them to be a match for my combination of endurance and strength. Once I crossed the line at my first Spartan Ultra distance ( around 50k, and often on mountainous terrain), there was no looking back. At 40 years old, in 2019, I participated in my first 12 hour, overnight, looped-style race. I had one goal: run 40 miles. I ran 45 official miles and managed to come in second place. I kept trying to see how far I could go on my own two feet. My longest race has been 103 miles.”
Paying it forward: “The idea for Take2Trail came to me when packing for the Javalina Jundred in 2025. I found myself digging though bins of packs I didn’t love, headlamps I no longer needed, shoes that didn’t work for me, and more. Around the same time, my closest running friend had a running belt she hated, so I offered to buy it from her. These experiences made me realize how much ‘stuff’ goes unused after a single experience. I wanted to come up with something that solved this, and Take2Trail was born.”
Helping runners and the environment: “Take2Trail gives people a way to keep items out of landfills and makes the sport far less expensive to try out and/or participate in. All of my outbound packaging is either recycled from inbound packages or sustainably produced from recycled materials. I use recyclable paper tape. The list goes on. I’m proving that a business can be built incorporating sustainability practices from the outset.”
Maria Rowbotham
director of production & marketing at Gather Events; host of the She’s Smart podcast
Building her own path: “When I moved to New York, I took a job in finance to pay the bills, and started styling friends and family on the side. I loved it. It wasn’t just about clothing — it was helping women feel powerful in their own skin. It grew into a 15-year business with wonderful, loyal clients. I loved styling — and still do — but about a year ago, I felt ready to stretch creatively. My friend Daniela had just launched Gather, her event planning company. Joining Gather felt natural; our strengths complement each other. Styling is where I learned to see detail, confidence, and transformation. But my focus now is building Gather and creating experiences that bring people together in meaningful ways.”
Lifting up strong women: “Over the years, I had the privilege of meeting extraordinary women. A real gift wasn’t just helping them get dressed, it was the conversations. I kept thinking more people need to hear these stories. So I started a podcast. I made a list of every woman I’d want to interview. I taught myself how to record, produce, edit. I started inviting women from my list, and they all said yes. The name ‘She’s Smart’ stems from the truth — the guests are the smart ones. I get to sit across from them and learn.”
Serving her community: “When we moved here, the Weston Women’s League was my entry point into the community. Co-chairing Main Street Weston holds a special place in my heart. I love Weston. Being involved has allowed me to build friendships and to contribute to something bigger than myself.”
Chelsea Elkind, M.S., OTR/L and Lauren Rosenblum, M.S., CCC-SLP
Co-founders of NeuroMind Services
Friends and advocates: “Chelsea and I met through a mutual friend while on maternity leave,” explains Lauren. “We had tremendous overlap in our professions, creativity, passion, and drive, and we realized it would be a great idea to join forces when we returned to work. We found ourselves daydreaming about building something thoughtful and empowering for the neurodivergent community, so, we started NeuroMind, a hub for neurodivergent people looking for mindful support that is affirming and comprehensive. Since launching, NeuroMind has grown into a multidisciplinary practice of speech-language pathologists, occupational therapists, counselors, and social workers serving neurodivergent individuals and families.”
Giving people tools—and empowerment: “My journey into deeper self-understanding began when I started approaching my own patterns with curiosity instead of criticism,” says Chelsea. “What once felt like personal flaws gradually revealed themselves as patterns I could learn from, anticipate, and work with. As I developed a deeper awareness of myself and how the mind works, I learned to replace self-judgment with self-compassion and began building tools, systems, and practices that support growth and empowerment. That shift became a defining moment in my life and work. [For me], success means building systems and strategies that work with our unique brains rather than against them. The most meaningful moments are when clients move from self-criticism to self-understanding.”
Part of Westport’s future: “This is the town that shaped me,” says Lauren, who grew up here. “To now contribute to its fabric, not just as a resident, but as a business owner, clinician, and mother, feels like a full-circle moment. I’m grateful to be building something mission-driven here and to give back through support, advocacy, and education. I’m proud to stand among women who are working every day to make Westport stronger, more compassionate, and more forward-thinking for the next generation.”
"Seeing everyone cheering each other on while continuing to do cool things and prioritizing family creates such a motivating energy.” -Ashley Holt
"What I do isn’t just massage, It’s about treating people with dignity, and caring for others when they’re vulnerable." -Christine Horelick
"Westport is a special place because it’s made up of individuals who believe in contributing to the rich fabric of our town." -Amanda Castellano
“I have had the privilege of meeting extraordinary women. A real gift wasn’t just helping them get dressed, it was the conversations." -Maria Rowbotham