Bob Gregory is this year's Milford Living Treasure

The Junior Woman’s Club of Milford will honor Robert Gregory — the man who came up with the phrase “Milford, a small city with a big heart” — as this year’s Milford Living Treasure.

A bit about Bob

Gregory, former community and economic development director, oversaw an era of change in Milford.

His office was involved in one way or another in helping to turn an old sewage plant into a city marina, transforming blighted areas into now prospering, attractive parts of the city, and creating new developments, like Lowe’s, where Milford Jai-Alai once stood.

Gregory retired last year after 21 years as the city’s community and economic development director. Before taking the city job, he was director of the Milford Chamber of Commerce for 19 years.

Although he was in public positions steering the city through change and progress, Gregory was most often very much the man behind the curtain, the man orchestrating mayoral inaugurations and city celebrations.

A Milford boy

Most often he was behind the scenes, except for perhaps when he was very young, just 8 years old, and standing center stage at Milford City Hall, reciting the Gettysburg Address, from memory, as part of a Daughters of the American Revolution program.

He was and still is very much a Milford boy. Back then, he was surrounded by Milford-connected family. His father was a postal clerk in town, and his grandfather ran a general store at the corner of Prospect and Cherry streets.

Life changed for the Milford boy when he was 10 years old: His father died. As a result, Gregory took on a lot of responsibility at a young age, including acting as a father to his younger brother, David, while at the same time finding a sort of surrogate father himself in a neighbor who led the local Scout troop. Scouting became very important to Gregory, and he went on to earn the Eagle Award, the highest award in scouting.

“Webster defines ‘patriot’ as one who loves his or her country and supports its authority and interests,” Kathleen Alagno, Chamber of Commerce president, wrote in her letter nominating Gregory to be this year’s Living Treasure. “He is a Milford ‘patriot’ in the truest sense of the word.”

Gregory left Milford for a time. He attended the University of Connecticut, where he earned a bachelor’s degree in speech and drama, and then he served as a 2nd lieutenant in the U.S. Army ROTC program through UConn, at Fort Belvoir in Virginia. There, holding true to one of his mantras that he’d rather throw a party than go to a party, he served as an entertainment and theater officer, organizing shows and entertainment for the troops.

After serving his tour of duty, he returned to civilian life with his young family, settling in Mansfield near UConn, where he took a graduate course in drama. He got a radio job with the Nutmeg Broadcasting Co., and eventually launched a new radio station in Southington.

Oyster Festival is born

Gregory left the radio station to direct the Southington Chamber of Commerce, and from there he got a job as director of the Milford Chamber of Commerce. He was an attractive candidate for the Milford post because he had just helped Southington organize an apple harvest festival, and Milford wanted to start a festival of its own.

When he arrived back home in Milford, one of the first things he did was start a committee with the late Bob Cooke and others to explore ideas for an annual festival.

“The committee met and was kicking around ideas,” Gregory said, and oysters seemed the right course.

“My mother used to tell me that when I was 3 years old I ran away to the oyster docks to see the chickens — which were really seagulls,” he said with a laugh.

Add to that, the oyster industry was once big in Milford, the native Americans had thrived on oysters, the National Oceanic and Atmospheric Administration has a laboratory here, and the oyster is said to be an aphrodisiac.

“So there was history and romance,” Gregory said.

And so oyster festival it would be, and it would be held the third Saturday in August because committee member Bob Young, who worked in the hotel industry, said hotels were always booked that weekend. It was when the New York Giants played their pre-season game in New Haven, and so people came from far and wide.

“That’s the reason it’s the third Saturday in August,” Gregory said.

That first year, festival organizers expected about 5,000 attendees, but they got 20,000 and ran out of food.

Gregory recalled that Bob Cooke looked at him and said, “What have we done?”

A tradition had been born.

Small city

It was while working at the Chamber of Commerce that Gregory came up with “Milford, a small city with a big heart,” to use on Chamber material.

“I thought it defined the character,” Gregory said.

Later, the late Mayor Fred Lisman brought the phrase to the Milford Board of Aldermen and asked the board to vote to make it the city’s official slogan, which it did.

Ushering change

When Gregory stepped into the post as the city’s director of community and economic development, he discovered a part of the job that really inspired him, and that was grant writing. Gregory got a crash course in helping city residents by securing government grants because a month after he took the job, Storm Beth hit, and he was called on to help the city and its residents repair storm damage.

“The storm hit on a Friday, and Mayor Fred [Lisman] called me on a Sunday and said, ‘You want to go for a little drive?’”

He, the mayor and several other officials hopped in a four-wheel-drive vehicle and drove through the Point Beach area and other parts of the city hardest hit. After that drive, he got involved in a government-funded house elevation program at Point Beach.

Ironically, storms bookended his career with the city. His last piece of work, before packing up his office last year, was to process a thick government application document for a homeowner seeking to elevate a home after Tropical Storm Irene and Hurricane Sandy.


Gregory has been involved in countless celebrations and community projects, from the Milford High School All Class Reunion to the city’s 375th anniversary, which he chairs.

He’s served on the city’s bicentennial committee, school board, historical society, Milford Progress, Milford Fine Arts Council, Milford Rotary, and a lot more.

Married to Elinor, they have seven children and 14 grandchildren. The family, community activity, gardening, and birding keep him busy today.

Many people know Gregory for being a man of many hats. He has a lot of hats, from a Mexican sombrero and a fez that he rarely wears to the ones he does wear — maybe about 40 — according to the season.

Many people may not know that he is a big Frank Sinatra fan. His favorite song, he said, is Young at Heart.

Living Treasure

Inspired by the Sante Fe, N.M., Living Treasures Program, the Junior Woman’s Club of Milford, under the guidance of past president Sara Baluha, established its own program in 1997.

In February the club accepted nominations for individuals aged 65 years or older, whose contributions and actions have enriched the community.

A Panel of Common Good composed of community leaders was formed to help make the selection.

A ceremony honoring Gregory will take place Friday, Nov. 7, at Milford City Hall. Residents are invited.

“We are very excited to honor Bob Gregory as this year’s Milford’s Living Treasure,” said  Tami Jackson, a past co-president of the club. “We look for individuals who do extraordinary community service in our city, and Bob exemplifies that criteria. His latest service to our community was chairing Milford’s 375th Celebration Committee. The number of boards and committees he has served on is too long to list, but I encourage residents to come to City Hall on Friday night to learn more about all that Bob has offered to the city of Milford.”