If you’re a Westporter, you probably know Mike Calise.
The 1958 Staples High School graduate and Marine Corps veteran runs the longtime and very successful Settlers & Traders real estate firm. He’s a frequent attendee at town meetings, making sure nothing slips through our boards and commissions’ cracks.
Mike Calise with his sweetheart, Sally.
You can find him almost any day — in any weather — at Compo Beach. That’s where he hangs out, by himself or with his extended family. He keeps a loving eye on it too.
Mike and his grandkids. Cookouts on the beach are a family tradition. The food often comes from Calise’s deli — the market his family established in the 1930s,.
Mike has a great back story. While still at Staples, he boxed in the New York Golden Gloves tournament.
While stationed at Camp Lejeune, he bought a 9-passenger Pontiac Safari station wagon. Each weekend he ran a North Carolina to New York transport service ($15 each way; 658 miles in 11 hours).
His mother Louise — of Calise’s market fame — packed a large bag of delicious meatball and eggplant sandwiches for every trip back.
Mike Calise, Staples Class of 1958.
As a Marine from 1958 to ’63, he was assigned to Force Recon — an elite group that was always first on shore. They trained with daily long distance runs and swims.
Mike started an Arnold bread truck route in 1963. He founded Settlers & Traders in 1967. In 2008, he received a Historic Preservation Award for the restoration of  his office building at 215 Post Road West. This year, his real estate firm celebrates 50 years.
For all his life — going back to his family’s stores on Post Road West and East — he’s been an important part of life here. He’s a longtime member of the Republican Town Committee; a former delegate to the state Republican convention, and served on the RTM and Architectural Review Board.
Mike loves nature, gardening and canoeing. No morning at the beach is complete without his “Compo Gumbo.”
He loves Compo so much, he’s got it on his license plate:
Mike cherishes his family: his longtime sweetheart Sally; his 5 children (Catherine, Sandra, Maria, Bettina and Frank), and 7 grandkids (Francesca, Trent, CJ, Reed, Charlotte, Cameron and Caleigh).
They love him right back.
As does the rest of Westport — the town he’s loved for over 70 years.
Mike Calise, in a familiar pose.
Mike and Westport, an unbeatable combination.
Congratulations Mike. This is a well deserved honor. Every time I see a comment from Mike I have wanted to ask…. Is that “our Mike, Staples ’58”? All his remarks have echoed the Mike that we all knew and respected. I have my answer. Yes it is the Mike we knew. Keep up the good work on behalf of our town, country and our families. You are a true hero Mike.
Leave to Dan’s blog to answer an 11 year old the mystery for me. As long as I’ve lived in Westport, I wondered who this wild (in the best possible way!) man driving this wild car on the streets of our town in summer is!
Loved this post.
Thanks!
Mike and I were both members of the Staples High School class of 1958. While Mike has been a long time member of the Republican Town Committee, I have chaired and have been a long time member of the Democratic Town Committee. Mike was on the RTM and ARB. I served on the P&Z, Board of Selectmen and Charter Commission. We both care deeply about Westport, and I appreciate all that Mike has done for our community. For the two of us, politics has never gotten in the way of doing what we have thought was best for our Town. .
Mark J. Marcus
One of the smartest and most knowledgeable Westporters ever! Congratulations Mike and Semper Fi!
Thank you for that story. I do not know Mike but I see him often riding his car (looks like an old Land Rover Defender but for some reason it has a Mercedes Benz logo on it) and I always tell my wife that I want to be as cool as this dude who never seem to wear a shirt, tanned as if we lived in Hawaii, driving that absolutely awesome car without the front doors and looking like he has not a single worry in his life.
When I grown I up I want to be like Mike! 🙂
Mike is a genuine Westport treasure, truly what the “real” Westport is all about. This post is terrific in introducing him to those who do not know him personally while confirming what we who have known him always have always known… a very smart, compassionate and caring person and a great friend to have! And, Sally too – a beautiful and gentle person, never without that super smile.
This was nice ! You’ll have to go to Compo🤔
Sent from my iPhone
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Nice piece, Dan. Besides being one of the shrewdest observers of local land use issues I know, it’s worth mentioning that Michael is a beekeeper as well. And no, I’m not going draw any parallels between those two subjects. Nope, not at all.
Oh, I miss Michael Calise so much! It was always a treat to see him at the beach and talk about preserving the Compo we loved. He’s smart, kind, decent and witty, and I loved this story. He really walks the walk. Thanks, Dan!
Didn’t edit my comment well. I *miss* him because Ken and I have moved from 60 Roseville Road to NJ. Might have been taken the wrong way. ;-(
Just tying it back to this morning… we had Calises cater the beach breakfast this morning. We love Carmine!
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A one of a kind, true legend!! Congrats Michael
What a great story. It brought back so many great childhood memories of stopping at Calise’s Market with my mother, to pick up The Daily News and the Norwalk Hour on the way home from her office. My father would not let a day go by without reading either paper, especially the Sports page! All the Calises were friendly and courteous even to us as kids!
Great Story. Mike Calise is a remarkable man who does so much for this town and he does it quietly and with class.
Thank you for serving our country Mike…and as a Force Recon Marine of all things….the toughest of the few and the proud.
Semper Fi.
I was Sally’s classmate at Staples. I’m glad that she and Mike have each other. Good people.
ADW Staples 1956
i always said hello to him. I never knew who he was. Great story. Revealing
Mike’s the best of the best, his love for the Town unparalelled, and his knowledge of planning and zoning matters unmatched.
Plus, he’s a hell of a guy wuth a heart of gold.
I was behind Mike in his jeep on the Post Road last week. I couldn’t get over how “cool” it is – reminded me of my grade school friend’s dad’s jeep that we “borrowed” when we were 12 when his parents were away. Always wanted a jeep just like that.
Mike is one of the good guys of Westport.
Mike Calise…a true gentleman, patriot and friend. Mike you are the best of the best.
Mike is a great man. Would give you his shirt of his back. He is Westport. Congratulations mike. Miss seeing you stop for coffee in the morning.
I first met Mr. Calise last year on the route 1 bridge. He was hanging over the railing, in the middle of a heavy rain and thunderstorm with high winds, clipping the American flags off of their poles – one by one – to be stored safely until the weather subsided to avoid their tearing. I stopped to help, I even got a ride in the famous “Compo” Jeep. An amazing person, definitely!
Great meeting you at Compo tonight! We’d love to send you a Townee tee – send us an email at towneeus@gmail.com and we’ll get that tee over to you.
Mike, you are a cherished guy!
The Calise’s are a tried & true fabric of the Westport community!
Great Story, Great Guy!
Has the coolest car in town, too.
Mike – you, your dog on two chains in the back of your overly vintage cheep and your leather hat are a symbol of Westport I don’t want to miss !
Michael Calise this is more than well deserved. Congratulations!
Nancy Marr’s daughter…
Love you Kelly Marr!! Special place in our hearts for always! xx
Man of integrity, honesty, and wisdome. A genuine American patriot and more…
Mike, All these wonderful comments are well earned. You contribute so much to what makes Westport the great place that it is. And a Marine too! Well, that certainly makes a lot of sense. Clearly you have never stopped serving. Thank you!
Semper Fi
For more than 40 years Mike has been a friend to me and my family . Fran , Anne ,Joe , Mary Anne and Peter Pastorelli. ..Mike brokered a deal with me and his aunt Theresa Gilbertie in 1972 where I created Pearls restaurant , now Da Pietros…Mike is a considerate great listener and a true lover of this town. I’ve “encouraged ” Mike to join Sally and I for yoga but Mike has already found ease , steadiness and comfort , his yoga.. He practices authenticity. ..Deep bow Mike for all you do ..
Mr. Mike Calise,
Congratulations!