‘Hometown Icon’: Bobby Peloso Turns 60

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Bobby Peloso of New Canaan. Photo courtesy of the Peloso family

Bobby Peloso became part of Marianne Perry’s life when she moved to New Canaan in 1979, though it would be many years before she met him.

Driving along Route 123, Perry would see Peloso standing each day on a grass verge off the east side of the state road, between Urban and Hill Streets, waving to passersby from the edge of a large garden.

“I remember always seeing this person,” Perry, for the past 14 years an Urban Street neighbor and friend of Peloso’s, told NewCanaanite.com. 

Bobby Peloso. Photo courtesy of Dave DiPanni

“He is just a delight. We still see him most every day. He is part of our lives. He is the best neighbor you could ever have.”

She added with a laugh, “He knows everything about everyone—which is good and bad, I guess. He’s a person that many of our elderly people in town who knew him and his aunt and uncle and grandfather, they still call him and gossip. So he’s quite a fixture.”

On Thursday, Peloso—one of New Canaan’s most visible and widely liked residents, known to countless local kids after more than 30 years helping out with the buses, recess and cafeterias at South School and Saxe Middle School—turns 60.

Originally conceived as a block party, a surprise parade-style celebration of Peloso’s birthday and singular place in the community is to be held Thursday evening. Organized by neighbors who describe their friend as a smart, gifted and loving man with a powerful memory, the drive-by event will see celebrants stage at East School at 5 p.m. (observing social distancing) and travel past Peloso’s home on what is forecasted to be a clear and sunny evening.

It’s an appropriate event for a man known to New Canaanites as a sort of unofficial “town greeter” for motorists zooming by on 123.

The eighth of nine children, he was born with special needs and grew up living between his Pound Ridge, N.Y. immediate family and aunt, uncle and grandparents on Urban Street in New Canaan, which would become his permanent home, according to sister Barbara Peloso. He attended a special education program at Royle School in Darien, finishing there at age 21 and soon settling into his position with New Canaan Public Schools, she said.

Asked what the birthday celebration means to her, Barbara Peloso said, “I could start crying.”

“It’s very emotional for me,” she said. “This is just a great tribute to him and what New Canaan is all about. They have all kinds of programs for seniors and he is fortunate he works at the school. They take care of him. I think it’s just great they are doing this. It is a whole other family. He has a network that is in place.”

Important parts of that network include neighbors such as New Canaan firefighter Dave DiPanni and longtime South School co-worker Judy Gilroy and her husband, Tom.

DiPanni, a 1985 New Canaan High School graduate, said Peloso has been a designated associate member of the Fire Department who regularly greets him around the neighborhood with a “See you round the campus” or “10-4, good buddy.”

“Bobby is just so positive with everything,” DiPanni said. “He has such a bubbly and terrific personalty and he just puts a smile on your face every time you talk to him.”

Peloso also has what DiPanni described as “an impeccable memory.”

He has memorized the birth dates, anniversary dates and employment start and retirement dates of New Canaan Police and Fire Department members, DiPanni said.

“Whenever I come off duty from the Fire Department, he will come across the street and inform me and say, ‘Guess whose birthday it is today?’ And he will remind me of things. It’s unreal. He even knows the details about all the trucks.”

DiPanni added, “One time he busted me at work. I was at the Fire Department with 15 minutes left on my shift and he came up to the firehouse and wished me a happy anniversary, such-and-such years and time. The guys were really busting my chops. ‘You worked on your wedding anniversary?’ ”

The DiPannis have Peloso over for holidays so that he’s not alone and, with the Gilroys and others, ensure that his home and property are maintained, that there’s food in the house and that he has rides when needed (Peloso himself doesn’t drive). 

Barbara Peloso said the Gilroys have taken over twice in recent years for long stretches as Bobby’s primary caregiver when she’s been set back by her own medical issues. 

Asked about Peloso, Judy Gilroy said that when she and her husband go away on vacation, they call him every day, “just to check on him and ask him the weather.”

“So he expects our call when we are gone,” she said. 

She added, “He has been like a brother to us.”

“Bobby is a familiar hometown icon. Everyone knows him. Everyone watches for him to wave to him. In the schools, they know going to work that he will do the buses, he will do lunch, he will do playground duty. And also to the young people in the schools, everybody knows Bobby. You grow up knowing Bobby. And he never changed and then you moved on but you would see him when you travel down the road. He’s just a New Canaan icon.”

Paul Gallo, a 1980 New Canaan High School graduate and lifelong Urban Street resident known to many as the wrestling coach at NCHS, said he has known Peloso since childhood. 

Though young Bobby didn’t venture out and play with other kids, the neighborhood children would gather in the Pelosos’ yard to play whiffle ball.

“He could hit the ball a ton,” Gallo recalled. 

“We used to try to hit the tennis ball over his house and sometimes it sort of hit the house. We got yelled at a few times, but he could put it over. I never could. I was too small. But he was strong and he had good hand-eye coordination. We use to go to Mead Park for tennis balls and go to his backyard and he used to whomp that ball over the house.”

Gallo described Peloso as a man with a big heart who likes to be social. 

“He goes and stands by the road and he enjoys just seeing and talking to people,” Gallo said. “He has been out standing by the road since he was young. He just likes the stimulation. He knows everything—my birthday, my mom, my brother—he remembers all that stuff.”

Asked what she believes her brother is thinking about as he oversees New Norwalk Road, Barbara Peloso said, “He kind of does a little inventory in his head. In his mind, the numbers—don’t ask me how that works, that part of his brain. He will tell you how many red cars went by. Connecticut plates. Like an inventory, taking attendance, checking everyone out. He is like the supervisor of 123.”

She added with a laugh, “He knows how to get out of doing things. When you give him a task, he either will not do it or screw it up so you don’t ask him again. He is my brother and I love him—and I want to kill him. Whenever you take him some place, he’s like the pied piper. He knows everybody. Go to Wal-Mart or Walgreens. ‘Come on, Bob, we gotta go.’ He’s very social.”

Perry said Peloso has forged a unique place in the South and Saxe communities.

“He sees the kids and teachers every day and they absolutely love him and celebrate him whenever they can,” she said. “I am sure many people from both those schools will be in that [birthday] line. They just love him. He’s just a fixture in a way, and someone you can count on. You can count on seeing him and those kids can count on seeing him. He’s in their lives and they grow up and then they drive by 123 and honk and say hello.”

Jen and Scott Chard, fifth-grade special education and eighth-grade science teachers at Saxe, respectively, said in an email that Peloso is “a treasured member of our Saxe community.”

“He is a living testimony to the good things that New Canaan represents,” they said. “His presence is always known and his wonderful personality is a breath of fresh air. He embodies all of our school values and is committed to both the staff and the students. Everyone in our Saxe family loves him.”

Barbara Peloso said the birthday plans and support for her brother reflect a fellow-feeling that defines the town. 

“I just want to thank everyone in New Canaan that treats him with respect,” she said.

30 thoughts on “‘Hometown Icon’: Bobby Peloso Turns 60

  1. Mike- This is so great. I always honk to Bobby at his post! and of course my kids have grown up with him at school. Thanks for painting a picture of him that I didn’t know before!

  2. Thanks, Mike for this wonderful portrait. I will be sending this to my grown children who will remember waving to Bobby.

  3. I’ve always waved to him without knowing who he was. When my kids asked who he was I always said he worked for the CIA and is monitoring New Canaan for the bad guys. LOL

  4. Our family lived on Route 123 for 10 years and often saw Bobby at his “post” beside the road waving and cheering on a passerby who he clearly knew well. Happy 60th Birthday to a New Canaan treasure.

  5. Happy Birthday, Bobby! We live just above the pond on East Ave and we thank you for your friendship via all the warm waves and smiles since 2008. Have a great day today! Join the club….60 years old!

  6. What a great article for such a great human being. And, he used to memorize license plate also !!! Happy Birthday Bobby !!

  7. When we moved to New Canaan in September, 1979 and lived on Laurel Road, I traveled up and down 123 almost every day. I saw this young man “at his post” waving to every car. After a few days, when my son and I saw him, I would honk, Rich would wave from the back seat. He was there in warm weather and in cold weather. Our honk and wave was a ritual. A bit later on I learned his name, Bobby, and a little bit of his story (can’t remember when or how). It was just a warm and gratifying feeling to know who he was and how loved and special he was to his community. I don’t travel much on 123 any more, so I haven’t seen him lately. But I was happy to hear he is still greeting drivers, and wish him a most happy 60th birthday.

  8. I grew up on Brushy Ridge and had the privilege of seeing Bobby frequently, waving to, and at times briefly chatting with him out in front of his garden. When he was not out in front for some reason, the absence was very noticeable. His presence just made/makes you feel good. Thank you for being the gleaming smile to so many, Bobby. Happy 60th Birthday, man.

  9. Happy Birthday, Bobby! You are one of the very special people that makes New Canaan a great place to live!

  10. I want to wish Bobby a very happy birthday as well! I’ve lived in Massachusetts for over 50 years, but growing up in New Canaan, and living on Smith Ridge Road, I saw Bobby waving to our car as Mom (Bobbie Bacon) drove by, and we kids (and Mom) always waved back. Mom passed away 7 years ago, but my son lives in New Canaan, and so I still drive Rte. 123 to see him and his family. I have often wondered about Bobby because I haven’t seen him for quite a few years, and I hoped he was alive and well, which now I know is true! Thanks to all who wrote comments that filled me in on a very special person who will always live in my memories.

  11. I grew up on the corner of Summer & Brook Streets and I can remember on summer nights Bobby, Elmer & Mary would take their after dinner stroll by my house as they headed up to the firehouse or just to sit with their gang in town. It was such a pleasure because they always stopped to talk for a bit to my Pop or other family members as they passed by.
    I can’t tell you how many times my out of town friends have asked me who the guy was standing on Route 123 waving to everyone! That’s our Bobby!
    He is amazing when it comes to remembering dates. When my father died we were trying to figure out the date when he first became a volunteer with the New Canaan Fire Department. Jack VanDeusen (sitting at my mom’s kitchen table) called Bobby up on the phone and in an instant got the information we needed.
    Thank you Bobby for your friendship for a long, long time. You are New Canaan’s gem and a true example of kindness to everyone you meet.
    Enjoy your special day today!
    Love Karen Tiani Hussey

  12. Happy birthday! Bobby always gives me a warm welcome when I’m at South and Saxe and my kids all love him!

  13. Happiest birthday, Bobby! My boys and I have always loved waving to you and seeing you when they were at South and Saxe. You brighten everyone’s day. Everyone has his own unique gifts. Thanks Mike for bringing the community that loves Bobby a little closer to him.

  14. Happy 60th Birthday. Cousin Bobby U Deserve All God’s Best. All The Wonderful Times Growing Up In NC When We Were Kids… With Grandpa & Grandma XO Michelle Garibaldi

  15. Happy Birthday Bobby!
    Sending you best wishes and blessings in your 60th year and always.
    ❤ Anthony and Lauren

  16. I met Bobby only 5 years ago because my daughter and son-in-law (Michelle and Dave DiPanni)live across the street from Bobby. We were celebrating my birthday (Dec 8th) and my grandson’s birthday (Dec 2nd) at 22 Urban St. Bobby was invited, as usual. Since then when I visit the DiPanni’s and Bobby is outside he always tells me how long before my next birthday and how old I will be. I find that remarkable! He is amazing and a very sweet person. I will be participating in the Parade. Happy 60th Birthday, Bobby.

  17. Remember Bobby from when his Grandmother and Grandfather used to watch him when we would go over to there house with my parents for a visit…that was about 50 years ago if not longer…then always seeing Bobby on rt.123 always waving and that smile on his face…hard to believe how old he’s gotten and how long it’s been…

  18. Happy Birthday Bobby! My family grew up in Peloso’s apartments from 1955-1973 when our parents, John & Glenna Stanton moved to Cape Cod my sister, Bev and I remained in the apartment till we married. We welcomed Bobby when he came to live with Pop, Angie, Uncle Elmer & Aunt Mary. The Peloso’s were wonderful people, we were part of their family.They always watched out for me and my sister. Lots of delicious Italian food, picnics and family & friends gathering in the courtyard. Pop could make anything out of wood and wheels that all the kids would ride or play with. They had the best veggie garden in New Canaan and Bobby always was helping his grandparents with it. We would stay outside till it got dark, those were the days. We were like the TV Show “ The Little Rascals” so fun. I could go on and on. HAPPY 60th BIRTHDAY MY FRIEND BOBBY 🎂🎈😊❤️

  19. Made a mistake about going over to Bobby’s grandmother and grandfather it was his great grandmother and grandfather on Urban St.

  20. Thank you for acknowledging this fine human being.Good to put a name to the face I have seen for many years..Thanks for the info regarding Bobby!! I live hear in N.C. for 40 yrs. Often wondered about this young man, and why he would be out there greeting people@!! Made me feel welcomed.Much happiness to you Bobby you are the kind of person that we should strive to become.Thank you for the love!!

  21. Bobby is the true meaning of “genuine”! He is what we all should strive to be, kind, friendly, generous and caring. I have known Bobby for 7 years now since I began working at Saxe. In the 20 years I have been involved as a high school coach in the New Canaan community, I would be hard pressed to find a better person than Bobby.

    Happy Birthday brother!

    Rich Bulan

  22. Happy B-Day, Bobby!!
    I missed your call on my b-day this year. Hope to talk to you soon. By the way, am I still in the running for your favorite Saxe counselor? Let me know! 60 is a great number, I remember it well.

  23. Uncle Bobby! He could hit a ball with a bat- it was unbelievable. Happy Birthday!
    John Peloso’s youngest daughter.

  24. Happy 60th birthday Bobby! I always remember Bobby’s smile and kindness from my days as a student at South School – and always waving to him on 123 as I passed by. Bobby has made such an impact on our community is the best way possible!

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