Meet Lindsay! - New Canaan & Darien Moms
📷 Michelle McNulty

Where are you from originally?

I lived in Los Altos, California for my early childhood; my family moved to Darien when I was nine.


What made you choose Darien over other towns in the area? How long have you lived in your town?

My husband and I chose Darien because we have loads of history here and we love being walking distance from the beach. My parents and my in-laws live locally, and we are all closely knit, so it was a bit of a no-brainer. (Also, we had the opportunity to buy my childhood home from my parents in 2007—they gave us a really good deal!)


How many kids do you have and what are their age(s)?

My three kids are 7, 6 and 4—a daughter and two sons. I’m totally biased, but I’m a big fan of theirs.


What are your favorite things to do with your kids in general or in town?

My absolute favorite thing to do with the kids: family bike rides. My husband gets all the credit for making us a biking crew—he was totally determined based on his passion for biking—and we have the best time tootling around town together. We wear our Camelbaks and just go on adventures, even in really cold temps. The best kept secret is Cove Beach (in Stamford) because you don’t need a beach pass as a non-resident in the off-season and it’s a huge, car-free loop for new bikers. We also love to collect treasures at the beach—each kid collects different odds and ends—and we can spend hours combing the sand and rocks. Another favorite is hiking at the Darien Nature Center, Woodland Park, New Canaan Nature Center and the Greenwich Audubon. We also love our regular visits to the Darien Library—we are SO lucky to have this superb resource. And a staple in our week is dining at Community Supper at Saint Luke’s Parish on Thursday evenings—it’s open to all. I love it because it folds us right into the greater community in a real and powerful way. My kids adore everything about it—in a few years, we plan to all volunteer there too. And of course, I always find joy coordinating with some mom friends and plopping ourselves at a park, beach, backyard or school playground for an afternoon while the kids play; it’s especially great when we order a pizza and eliminate making dinner from the evening’s routine.


What are your favorite events or favorite season in Darien and why?

I’m a summer-loving girl and The Fourth is my all-time favorite holiday. I’m a total sucker for the town parades on the Fourth and Memorial Day. I love the annual Where’s Waldo hunt that Barrett Bookstore hosts every July, the summer reading program at The Library and Sidewalk Sales. We love picking berries at Jones Family Farm and come Fall, pumpkin picking at Warrup’s Farm. The Darien Road Race in September is a family fave. I also adore a snowy winter (before the lingering gray coldness of March sets in). We love tailgating with hot cocoa and popcorn at the annual Christmas tree lighting at the Darien Sport Shop with friends. We’re happily involved in the community at our church, St. Luke’s—there’s always some enticing speaker, event, program or volunteer opportunity on the calendar.


Three things in Darien that you can’t live without:

Darien Library, St. Luke’s Parish and Pear Tree Beach


What has been the most difficult age with your children to date? What helped you overcome the challenges at that time?

I think 12-20 months is just plain HARD. They are a total danger to themselves as new walkers; they are frustrated and vocal with their verbal and physical limitations; and as the parent, you can’t take your eyes off of them, so it’s utterly exhausting. Saving grace? Friends with kids the same age. We teamed up and shared the experience—the whole village thing.


What is one piece of advice you would pass along to other moms? What was the best advice your mom gave you?

Be mindful of your spirit. It’s easy to ignore it when we’re responsible for so much. The mom in you is valuable, but it is not all of you. Plant seeds now to tend to the later you, when the mom responsibilities won’t be nearly as demanding. My mom is a huge presence in my life and still offers me valuable advice. The most pertinent advice to me these days is to take good care of my friendships. So true—nurturing those precious friendships and being open to new friendship keeps me afloat in many ways.


What have your children taught you about yourself?

So much!! But each one stands out in a specific way in how I reflect on my personal growth since becoming a mom. My oldest child is a believer in the unseen magical world around her, and I love being on the ride with her. In a sense, her unwavering beliefs in unicorns, fairies, mermaids and such have encouraged me to align my lifestyle with my deeply held beliefs. My youngest child has forced me to thicken my skin. I’m naturally quite sensitive, and there’s nothing like a strong-willed, opinionated and direct child to force me to toughen up and not take everything personally. My middle child has taught me to live in the moment and relish the joy of play. He’s imaginative and engrossed in the world he inhabits. Because of him, I slow down, investigate details with many of my senses, ask more questions and express my joy unabashedly.


What was your career before having children?

I taught tenth and twelfth grade English at New Canaan High School for eight years. In the summers, I was a dean at Phillip Exeter Academy’s Summer Program.


How has this community been instrumental in getting you to where you are now? In countless ways. I have mentors and support all over this town. From the core group of friends I met through my first child’s YWCA’s baby playgroup to the women at the Tuesday MOMS group at St. Luke’s, to my family and their local friends to the childhood friends I’ve held dear, to my former colleagues, I’ve feel supported, and that’s instrumental to my happiness and growth.


One thing people would be surprised to know about you… I’ve performed three weddings for friends! (I got ordained online.)


Inspired by… podcast listening. I’m happy to exercise when I have Brené Brown, Marie Forleo, Amy Porterfield, Brooke Castillo, Guy Raz, Ira Glass, Oprah and any of their guests filling my ears and mind.


Are you involved in a business venture, a local organization, a creative endeavor, or in the corporate world?

Yes! I founded The Trellis in January of 2017. I design and facilitate workshops and retreats. My signature workshop is for moms who have been home full-time and are looking to figure out What’s Next? for themselves, in terms of intellectual, personal and professional growth. Women leave the workshop with a personalized career re-entry plan, loads of motivation, meaningful connection with other women in the community and a greater sense of purpose. I love leading this workshop and welcome any mom who wants to figure out what’s next for her professional self to join us beginning September 28th in Darien!

I also co-lead a workshop called Beyond High School, where were tackle the college essay and much more. I put my skills as a former English teacher and my love of the adolescent age group to work in this workshop, and I’ve teamed up with local career consultant, Brooke Fisch, to lead it. The next one begins on September 24th for high school seniors. More can be learned about the workshops on the website: Join us!

What’s Next?

a workshop


Fridays: Sept 21st*, Sept. 28th*, Oct. 5th, Oct. 19th, Oct. 26th (added)


Located in Darien

*Come to the first session. If you like it, sign up to continue. No payment required unless you choose to continue. Use the code: DIPPINGTOE in comment box at registration.

Lindsay has inspired our “Personal Growth & Fun for Moms” Resource page! Click icon below and check it out.

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