For generations, the story has remained the same.
Young people who grow up in Westport get a great education. They participate in tons of activities. They are guided by teachers, coaches, clergy and neighbors. They are nourished by the town’s strong sense of community and history.
Then they graduate from Staples High School, begin lives elsewhere, and return only for reunions, and/or visit their parents.
But for generations, there is another chapter too. Not everyone leaves.

2nd Selectwoman Andrea Moore is a Staples grad.
Russ and Isabel Blair, Michael Calise, Bill Mitchell, Pete Jennings, Sam Gault, Jim Ezzes, Pete Romano, Darcy Hicks, Josh Koskoff, Jimmy Izzo, David Waldman, Andrea Moore — all are sons and daughters of this town who stayed, built careers, raised families, and continue to give back to their home town every day.
It’s not surprising that those once-and-still Westporters — whose ages range from their 50s to 90s — remain. They had reasons — like business and family — to stay.
But there is a younger cohort too that did not follow classmates and friends to Manhattan, Brooklyn, California, London, or countless other destinations.
Representative Town Meeting member Andrew Colabella keeps his eye on every aspect of town.

Jaime Bairaktaris
Jaime Bairaktaris works at Earthplace, volunteers with Emergency Medical Services, and runs The Westport Local Press.
Maxx Crowley joined his father and older siblings at SCA, the commercial and residential brokerage and management firm. Now he’s president of the Westport Downtown Association.
Patrick Duffy is here also, helping his father Tom and ready to take over his plumbing business.
That’s just a short list, off the top of my head. There are dozens more.
Let’s hear about them. Please click “Comments” below to give a shout-out to other never-left or came-back-to-town Westporters, of all ages.
Especially those in their 20s and 30s, who will help make “their” great town even greater, for decades to come.
(Hat tip: Karen Jennings)
CHEERS To ALL! -Adding Dylan Curran, age: early 20’s – 4th Generation Westporter. Living, and loving working: The Porch @Christies, Westport Booksale Ventures, Norwalk Hospital, and helping at Westport Police Department.
My father James Kinnally who has owned an insurance business in town for 40+ years and yes insures most of the old timers 50’s-90’s here because they know even at the age of 83 that he will get them the best deal on insurance for their personal and commercial Insurance and myself in my 50’s and grew up here and now raising my two boys thru the WPS system (one is on track and field team and the other is football and soccer kid). I raised them here because of family, friends, community, school system, downtown, and Longshore (where my son worked last summer and will be working as a sailing ⛵️ instructor this summer) our beautiful local Compo beach (that I spent my high school years and beyond tanning and partying and then taking my kids to every weekend and our Sherwood Island state park (my mom’s favorite place to go walk everyday until her death last year). But the best part are the people from back then. We rally around each other and support each other and help each other and laugh and cry together. It is truly a beautiful and unique town. And I am grateful to have been raised here.
Liz and John Videler! Both living and working here, raised four kids.
Greg Wolfe here still too. He and Todd Cummings have been in a local band together for decades.
Accidental Breakdown!!! Yes, Greg, Todd, John, Liz, and so many more…we are blessed to all have grown up here pre “three car garage” Westport.
We all embrace the change and all try to do our best to contribute to our wonderful community.
What a nice article Dan!
Here are a few more SHS classmates to add:
Stacie Curran! She has given more volunteer time and energy to Westport than almost anyone. Her list of involvements is too long but recently she was integral on starting Club 203 which brings together adults with disabilities for much needed social events at local venues like the Senior Center, MoCA and Earthplace.
Julie Whamond also involved in so many local organizations including the Westport Young Woman’s League and Staples Tuition Grants. She recently joined the RTM.
Todd Coleman who served as President of the Westport Soccer Association.
Doug Fincher has served on Staples Tuition Grants and the Christ and Holy Trinity vestry among others.
Dan and Nicole Donovan who have been involved in a number of local organizations while raising six kids in Westport.
Chris Tait who is a long time RTM member and started the successful movement that saved the Old Mill Deli.
Kim and Warren Bird
Kim and John Porio
Matt Porio
Tom and Veronica Hofstetter
And my husband Dave Moore who is also a “townie”.
There are so many of us still around and I think it’s one of the things that make Westport so special. I hope our kids feel the same way and want to raise their families here.
I was raised in Westport. My parents moved here with me and my sister from Norwalk in 1972. My dad, Dr. Arthur Brovender, was an orthopedist and had his practice in Norwalk. I graduated from GFA in 1986.
My husband, Art, and I bought the house I grew up in from my parents in 2005. Our son, Will, graduated from Staples last year and is a freshman at Berklee College of Music. My youngest son, James, is a freshman at Staples.
We initially moved back to Westport to be closer to my stepdaughters who were living in Weston. Coincidentally, after we decided to buy the house from my parents, I found out I was pregnant with my son, Will. Although there have been many changes to Westport since I was a little girl, it’s still a great place to live.
My family moved to Westport in the mid 1960s and ran a business here called Leisure Unlimited on the Post Rd where the newly built Pottery Barn now stands. Having returned to Westport in the 1990s I am proud to also have a business here since 2002 — Pilates for Every Body. Everything changes including Westport, but there is still no better place to live.
Who else is missing? YOU. Dan Woog has stayed, heads the list, bears witness, and tells Westport’s story like no one else could.
Thanks Werner for saying it. I thought of you, Dan, as well. Right away. You stayed and have recorded and preserved the stories of all of our lives here in Westport. You are on the top of the list!
John F. Suggs
Patty Kondub
Stew Leonard
Miggs Burroughs
Don Rice
Rick Burke who owns Burke Construction. Kevin Clark a private leer jet pilot, Mark Pocious retired cop, Buck Iannacone who owns Perfect View Landscaping, Joey Bottone of the Town Public Works, me! And I am sure many others, We came back or never left because we love our roots! And as mentioned above DAN WOOG!
John Suggs, I floated the idea once of referring to Westport as “Woogport” one day a year, on Dan’s birthday! I think I’ll e-mail First Selectwoman Tooker to see what she thinks about my idea.
My family has deep roots in Westport: my kids are the 8th generation of Nashes to grow up in Westport, though we actually go further back to before Westport was incorporated. My parents, Lloyd and Kris Nash, and brothers, Dan and Tim, are also still in town. My dad, Lloyd, is an active member of Christ and Holy Trinity Church, celebrated for his annual beef roast, and was a cub scout den and pack leader. My mom, Kris, was an EMT, beloved children’s librarian at Westport Public Library for 35 years, CPR trainer, and member of CERT. My brother, Dan, worked as a Beach School counselor and at the Westport YMCA and married Nicole Altbaum (another native Westporter, whose father, Dr Robert Altbaum is also a town fixture!), and they are raising their kids here, too! My other brother, Tim, along with his wife, Belkis, own Nice Threads here in town, providing T-shirts and logowear for many local schools and businesses, including Staples Players and Westport Pride. My husband David and I own The Great Outdoor Toy Company on Kings Hwy North, selling swingsets and trampolines since 1991. I love Westport, and I am so happy that I was able to raise my family here. : )
Kerry Long – Players
David Roth- Players
Tracy Flood – CLASP Ex Director –
Michael Bennecke – Artist
All come to mind immediately – and I will think of more as I go about my day! The Town is filled with talented “hometowners”!
Priscilla, II know this is a long shot, but I knew a Herb Long and he had an older brother that graduated in 1958 from Staples. Any relation?
James L. Long, class of 1958, captain of the Football team senior year.
There was an exchange student from Naples, Italy at Staples in 1958 and I visited him in 1968. I believe Mary Sargent was in the class of 1958 too. I can’t recall the Italian student’s name, but he was very popular! (Fabrizio Vitale maybe???)
Liz Heyer is another person who was excited about the opportunity to get involved and contribute to the community when she moved back with her family. Liz has served as vice chair of the Board of Education and is now running for Board of Finance as well as being involved with other organizations. Her involvement has been a great asset to the Westport community for three generations as a student, parent and having a parent living in Westport. This prospective is valuable when planning for Westport’s future. Janet Albert
One I forgot-
Dixie Webb O’Brien – mega-volunteer (STG, NCL etc) and all around good human and townie
My longtime friend and neighbor…John McCarthy.
Let’s not forget all the town employees who have been here for generations with both parents and children working to keep this town running. If I start naming I’m afraid I might forget someone. There are so many. Thank you for being here
And Brandon Pacillio he stayed in Westport and Sam Arcoli who was deputy police chief for a long time in our town of Westport and his son little Sammy and big Sammy and Joey Arcoli please don’t forget about them dan from sal liccione
thank you Dan , this is a great story and the people contributing to this story are awesome too. Hope more people add to this list too,a lot more people to mention.
Westport is a special town because of all these people, and especially because of you dan and your dedication to reporting not just news but about the people in town.
Chris Urist who was once the youngest member of the RTM until he started his family, now three children, 4th on the way.
Don’t forget Sam Vail, Rob Stone, Karla Clouser (Westport adjacent but works in Westport), Doug Bernstein, Phil Ross…the list could go on and on 🙂
As a somewhat newer resident I cannot speak to what it is like to be a lifelong Westporter, but obviously Westport and Staples has nutured and produced a wonderful dicotomy of individuals who have continued the history and accomplishments that are.the cornerstone of a great community.
I am also a bit saddened by the fact that the state of Connecticut has not been able to create a dynamic economic business and technology enviroment where a much larger percentage of the amazing educational emphasis and opportunity has not been able to retain as residents more of this great crop of graduates.
We are bleeding off to much talent with our unhealthy lack of innovation based industry. JMHO
Within the current group of PTA presidents, I think five of us are Staples grads and/or married to one. Jacque Haberstroh (CES), Nat Smitobol (SES), Allison O’Dell (SES), Elena Caggiano (SHS) and me (BMS).
1. Robin Tauck
2. Ginger Gault Donaher and her husband Jim
3. Lisa Floch Adelman
4. AND last but not least Westport PD’s illustrious Dave Eason!
… and what would Westport be without Ann Sheffer, eh?
Let’s thank the Nash family, their ice house, water wheel, and their lands around the Mill Pond.
I always find it interesting that people thank the people that were active from the mid 1800’s , and not the original founders.
Each generation recreates their own history.
While voting today I was approached by a pundant that wanted me to vote for a “Native” that had lived here for 12 years!