Meet Mark! - Westport Moms

The Gilrain-Lennon Family of Westport


Meet Mark Gilrain, a Westport father of twin 16-year-old sons and a local real estate agent. He and his family moved here from New York City in 2011, because they love how “Westport is relaxed and inclusive, and it has an excellent lifestyle for friendship, eating, and activities.” Read more about Mark and the Gilrain-Lennon family.

Do you work and/or volunteer? If yes, please tell us where and what you do.
I work in the Westport office of Brown Harris Stevens, a real estate brokerage that serves New York, the Hamptons, South Florida, and Fairfield County. I am a residential agent in the office, and I love it – the houses and people!

How many kids do you have, and what are their ages?
My same-sex spouse and I have twin 16-year-old sons.

Where do your children go to school, and how did you pick their school?
After finishing Saugatuck Elementary School and starting at Bedford Middle School in Westport, we found St. Luke’s School in New Canaan, where they completed middle school and are now in 11th grade. We looked at a few schools. When choosing St. Luke’s School, the immediate thing that stood out to us was the small class sizes. The classes are all conducted in a discussion-based Harkness format that emphasizes developing each child’s intellectual participation and engagement. St Luke’s also asks each student to participate in after-school activities, free-period clubs and associations, and service endeavors. When our sons saw the range of offerings, they were so excited to participate. The admission process itself was also very supportive, and St Luke’s has been a community and source of growth for our sons and our family.

What about your school makes it right for your family?
We are grateful for the small classroom sizes — only about 10-14 students per class and less than 100 students per grade — the excellent academics, the robust extracurriculars and sports, and the help and support from the college counseling office in selecting the right college. One of our sons competed around the country in Public Forum style debate. Our other son enjoys taking computer science classes and participates in cross-country and squash.

When did you move to Westport, and what led you to settle there?
We moved from NYC to Westport in the summer of 2011. The town is commutable to the City, has coastal amenities, is relaxed and inclusive, and has an excellent lifestyle for friendship, eating, and activities.

Mark with his sons.


What are your favorite family activities in the area?
We’re not great at it but enjoy playing tennis at the parks and rec courts. We like to go to the beach on summer afternoons and are great supporters of all the different local restaurants!

Name one thing people would be surprised to know about you.
When broadcast television was still more of a thing, Connecticut Public Television aired a Saturday evening program from New Haven called High School Bowl. Each episode set two teams against each other, answering trivia questions. My two teammates and I from Avon went down to a team from Fairfield, getting eliminated early in the season — but it was fun!

When you need “me time,” what are your favorite ways to escape?
I like to lift at the Edge, run on the treadmill or outside, or walk in the Haskins Preserve on Green Acre Lane. I’ve also been running early on Tuesdays and Thursdays with the NYRR/Westport-Weston YMCA training group.

What’s the best advice you’ve received from another mom/dad?
Make sure your kids know you believe in them and then believe in them.

What is your favorite place in town to:
Have dinner: Dunville’s
Go out for a special occasion: The Cottage
Spend time together as a family outdoors: Our backyard
Grab coffee: Dunkin Donuts
Shop for the perfect gift: J.Crew

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