Back in Town


Thank you Palmer’s Market for sponsoring our cover feature.

By PAMELA DEY VOSSLER

You don’t choose where you grow up. You do, however, choose where you raise your kids (for the most part) and live your life. And while there are no official counts, scratch the surface of many a Darien resident and you’ll find heaps of Darien High School (DHS) grads who have chosen to come back to their hometown to do just that. 

“The number of people in and around Darien that I went to high school with is incredible,” said Greg Grambling, DHS Class of ‘99. He returned to town 10 years ago with his wife Katherine, who grew up in Cincinnati. They are raising two daughters and a son here.


Why the mass return? 

“We were always like we’re never coming back,” said Kelly Marchesi Dillon, DHS Class of ’06, laughing as she recounted a story about starting an email chain to get old friends still in the area together for dinner and finding 24 of them. Kelly moved back to Darien in 2018 with her husband, New Jersey native Henry Dillon, right after they were married. They have two sons, one nearly four and the other 16 months old. “I think it’s one of those things where you need to get out and spread your wings. But once you do, you realize how good it was here and how comforting it is to be back.” Spreading her wings included college in Ohio, where she met Henry, six months traveling throughout Southeast Asia and a bunch of years in New York City (NYC).

There is also nostalgia. “It’s so special to be able to share things that we used to do growing up with (my girls) now,” said Tim Stisser, also DHS Class of ’99, who moved back to Darien from NYC in 2012 with his wife Lauren, a Wilton native, just before the oldest of their three daughters, now 12, was born.

When he wasn’t on a field, a court, in a pool or working his paper route as a kid, Tim was with his neighborhood pals playing street hockey, capture the flag and manhunt, or fishing and riding bikes—things he now does with his girls on “daddy dates.”

Comfort and nostalgia aside, there are as many enticements to live here for those who come back to Darien as for those new to town.


There is the commute to Manhattan, certainly. With fewer stops, the train takes the same amount of time from Darien as the ride from the geographically-closer Greenwich, as Tim pointed out. 

Another draw? The beaches and Long Island Sound, for sure. Plus, the taxes are lower, the schools, the homes, the clubs and nonprofits, the sports—for all ages, are incredible, and with commerce centered along the main roads, the ecosystem of parks and protected spaces in the outer reaches of town are beautiful. What’s not to like? Darien checks many boxes. 

….and there’s such a range of activities for our kids—all there to help our children find what calls loudest to them. It’s remarkable what we pull off in these 13 square miles that nearly 22,000 of us call home. 

Still, there’s more, and in this lies the true magnet that brings so many back (and keeps so many newcomers here). 

There’s a certainty to living in Darien, a connectivity and way of living in community that runs in direct opposition to all that would divide and isolate us in today’s world. The people who grew up here and come back recognize the common denominators in our shared humanity and flock to them, old school as many of them are.


“I live on Hollow Tree and it’s not necessarily a neighborhood but with eight to 10 houses around me, we’ve created a neighborhood,” said Tim who grew up in tightly knit neighborhoods on Walmsley Road then Briar Brae Road. “Some people have young kids, some don’t. Some have dogs that you give a biscuit, some don’t. I deliver barbecue to my neighbors. I always cook too much, and we knock on doors when we run out of eggs instead of running to the store. We look out for one another. It’s wonderful,” he said. “Our friends are like family,” he added.

“Darien has such a strong sense of community,” agreed Dana Ryan Kelly, DHS Class of ’04, who moved to Darien in 2017 with her husband Brian, also DHS Class of ’04. She grew up in Noroton Bay then northern Darien, playing lacrosse through high school. Brian grew up near Cherry Lawn, the friendly boy who waved at everyone who passed his yard. 

“Everyone was always waving, so I just waved back,” recalled Brian, laughing.

They returned to town by way of one year in Colorado (Dana), two years in NYC after they got together, two more in San Francisco and then back to NYC for another year.

“I had a very strong suspicion we would end up right back in Darien,” said Brian, who played golf and hockey through high school. They’re raising two sons and a daughter ages 7, 5 and 2 in the Noroton Heights part of town. 

“I love it more every year,” said Dana of her neighborhood. “There are just so many great families. It’s like a little city. At night, you see everyone walking their dogs and you see people’s families growing,” she continued. 

Dana’s younger brother is across town. Her parents too. Brian’s younger sister and parents are in Darien as well. It’s a nice way to live, with frequent flybys.

“I just stopped by my mom’s with my kids,” said Dana who runs Blue Shutter Design, an interior decorating firm she founded three years ago. “They love that more than anything. I feel like it’s making their next chapter so much better,” she added.


The certainty of Darien comes from living multi-generationally—through our families and our faith communities, the clubs and organizations we join, through our sports and other activities, and through giving back, contributing in ways big and small, participating in our kids’ lives and
in the lives of the kids who cross our path—as coaches, mentors, teachers, troop leaders and more, taking our turn at the wheel of the nonprofits in our area and all that drives our town civically in positions both elected and appointed. It comes from caring.

Is the road always smooth? Certainly not. We all take our licks from time to time. 

But when you are known, and know others, when you live in a place where you can still borrow a cup of sugar from a neighbor, where your friends—new and old—become an extended network of honorary aunts and uncles to your kids, a place where you belong, where even the worst days or any manner of self-doubt doesn’t hold up in the face of the familiarity you find as you make your rounds through any of the independent local businesses who do so much to preserve the ethos of this town …when you live like this, there is a strong foundation from which to handle the hard stuff that hits our lives, to celebrate the good stuff, try new things and grow.   

“Having that reassurance that you belong somewhere allows you to grow at the same time. That might be a little contradictory, but I do feel there’s something in that, at the heart of this town,” said Kaki Dudley McGrath, DHS Class of ’03. She returned to town in 2011 when she married John McGrath, who grew up in Boston. The two met at Columbia University where they both swam competitively. They are raising three sons, ages 10, 8 and 4, as Kaki continues to develop Dudley-Stephens, the clothing company she started with her mom and sister nearly 10 years ago. 

“Growing up, I was confident, but I was shy,” said Kaki, a top swimmer all four years at DHS and a co-captain her senior year. “Since my sister and my mom and I started this business together, I’ve been having to do public speaking, and go outside my comfort zone more than normal. But, being back in town, having that foundation and that reassurance, putting myself out there isn’t as scary as it once was,” she continued, sounding anything but shy and quiet.  

It’s a certainty that stands the test of time, and change. 

“In terms of the neighborhoods and the community participation, not a lot has changed,” said Tim.

“There’s such camaraderie here. It’s always been here and it’s definitely still here,” agreed Dana.

“There’s such a history and tradition in this town, but I also feel like we’ve been able to adapt to modern times too. I mean the three huge developments that are going on now are a testament to that,” said Kaki, referring to Darien Commons, the Corbin District and the new Noroton Heights project. “It’s not the same small village that it used to be. We’re adapting to new retail and new ways of living but we still have the traditions at the foundation of it all,” she explained.


It is a certainty that welcomes new ways of thinking.

“I know that Darien has ebbed and flowed over the years with people feeling safe and secure in terms of the LGBTQ community, academics, sports and social pressures, and of course mental health,” observed Kelly. “But I’ve seen a lot in the Darien Moms’ Facebook group and just in the news about trying to foster an environment that is aware of the challenges that our teens and other kids face, to create a sense of community around it so that our kids know it’s not a taboo thing to feel certain ways or to get help if needed.” she added.

…and it welcomes those new to the community. 

“I think people really have pride in making sure new people are enjoying the town and community as much as the people that are from here,” said Tim. When you love something, you want others to love it too.

Together, the new and old combine to become the keepers of a culture that bolsters our kids, giving them resilience and confidence, as it boosts us in our day to day lives.

But it doesn’t happen in a vacuum. 

It can’t be a one-way street,” said Greg, an elected member of Darien’s Board of Education. “I had the benefit of getting an incredible education through Darien and giving back through service to make sure that not just my kids but all kids who come to Darien have the same opportunity is really important.” 

And in giving and participating, you not only create community and shore up all that makes Darien the place it is, you get so much back. “I know a lot of people in town,” continued Greg, a racquets enthusiast who played tennis for the team at DHS all four years. “It’s not because I grew up here but because I play a lot of paddle and coach my kids’ sports. You meet people by being involved.  Volunteering through the church, schools or something else, there are so many ways to make new friends and be ingrained in our community.  All of those are critical. You give, and you get back because you’re part of something you care about,”
he added.

At the heart of it, “People want to know one another, and everybody is involved in some sort of community organization,” said Tim.

It’s where we thrive as human beings and it’s how our kids grow up to have the best shot at the kind of lives we hope for them.

Not everyone has a great experience growing up in Darien. Not everyone comes back. It can be a bubble with a wealth-based value system that can sometimes run counter to the truth of the town. There’s also a competitive drive that can be damaging for our kids if left unfiltered by the trusted adults and parents who are raising them. But it’s nothing that Darien’s culture of family values, belonging, giving and living in community, and the people behind it, can’t handle. 

 “So many people come back. It just shows you what a great town it is,” said Kaki.