100 Years After its Founding, Winter Harbor Agency Continues To Be Operated by Tracy Family
By Aaron Porter of The Ellsworth American

WINTER HARBOR—One hundred years ago, when the town of Winter Harbor was only 3 years old, one of its founding fathers, Bedford E. Tracy, was busy producing another offspring—the town’s first insurance agency.

Although generations of Tracys and others have come and gone from the agency and the town, both still thrive. One hundred years and four generations of Tracys after its founding, the Winter Harbor Agency is still operated by the Tracy family.

By all accounts, Bedford Tracy was a formidable man. He was a lawyer and civic leader in the community that was to become Winter Harbor. And if records are to be believed he was one of the prime movers behind the creation of the new town out of what was a corner of Gouldsboro. Historian and former Winter Harbor Town Manager Allan Smallidge said Bedford Tracy’s name appears on numerous documents associated with the creation of the town.

Smallidge said the community of Winter Harbor came into its own as the affluent summer community on Grindstone Neck started to flourish in the 1870s and 80s. Summer homes and the Grindstone Inn created a small economy of support staff and service providers. Smallidge said the resort became the mainstay of the local economy supplemented by winter fishing and labor.

He said his understanding is that property taxes in the Winter Harbor area of Gouldsboro went way up but were not necessarily reinvested in the betterment of that area. In the 1880s an effort headed by local business interests came forward with the plan to make Winter Harbor a separate municipal entity. Smallidge said Bedford Tracy worked toward that end. But his perceived prominence may simply have been the result of his having been a lawyer and therefore the most appropriate person to sign the paperwork associated with the change.

Whatever the case, the elder Tracy was a booster for the new town. He and other investors bought a plot of land across from the Masonic Temple and erected what, in the parlance of the time, was called a “block.” The Tracy and Bunker block, completed in 1888, housed a number of offices and shop fronts including the insurance company Tracy started in 1889. He continued to sell insurance and practice law until his death in 1912. Smallidge noted that Tracy accomplished a lot during the 48 years he lived.

Upon his death the operation of the insurance company fell to his widow, Rubie J. Tracy, and the name of the agency was changed to the Rubie J. Tracy Agency. This blatant use of a woman’s name as the head of a business venture was bold for the time. If a woman did run an operation, often she would sign and print her letter head with initials only so as not to reveal her gender immediately. Rubie Tracy did no such thing. Even her promotional calendars hid nothing of her identity.

Photographs of the widow captured a serious, bespectacled woman with a dignity about her that some who remember her still recall. But her life was not easy. Widowed at 47, she continued to run the insurance company for 33 years until her death at 82. She moved the operation once in 1915 after the Tracy and Bunker block burned. It may seem like the height of ironic bad luck that an insurance agency should be burned out, but Rubie J. Tracy took it in stride, shifting the office to the house her husband had built on Grindstone Avenue just past the golf course.

Earle B. Tracy Jr. said he remembers spending summers in the house with his grandmother. He said the center room on the ground floor was the agency office. He recalled the big wooden double desk that dominated the room, which was also populated by filing cabinets and a clerk. Smallidge said he recalled Rubie J. Tracy living in the house and running the agency. He was hired to mow the lawn and dig flower beds on the property.

“She was a grand lady,” said Earle B. Tracy Jr. who would come with his father from North Andover, Mass., every summer. “Dad would take her out because she wouldn’t drive,” he said. They would go visit aunts in Bangor.

He said his grandmother lived in Bangor in the winters from the mid-30s until her death. But she still ran the agency.

Earle B. Tracy Sr. left his teaching position in Massachusetts to take over the family business in 1945 when his mother died. His son, who was in the merchant marines at the time, still remembers that night.

“The night she passed I was in a storm going from Nova Scotia to New York only 15 miles out from here. I can remember that just as well as not,” he said.

Rubie J. Tracy’s name has not disappeared from the town since her death. The local Chapter of the Eastern Star, a women’s benevolent society, is named for her: Rubie Chapter 31.

Earl B. Tracy Sr. made some changes when he took over the agency. The business was moved from the old home on Grindstone Avenue to the old James Bunker residence in South Gouldsboro on Route 186. And although that move put the agency squarely in Gouldsboro, the name was officially changed to the Winter Harbor Agency for the first time.

He started conducting business from the house but built an office in the attached barn.

His son said the picture window that was installed in the office is still there with a view out Frenchman Bay to Mount Desert Island. He recalled that when his father first made the move it took six months to have a telephone installed. “For a phone we had to go across the road to Frank Gerrish’s house,” he said. But the business survived the move and grew.

Earle B. Tracy Jr. said 1945 was the first year real estate was added to the list of the agency’s functions. Since then it has played a constant but subsidiary role in the company’s life. He said it does mean that the office has to keep someone with a real estate license on staff.

Starting in 1947, the agency also prepared income tax returns for individuals.

“That kept us busy from January to April,” said Earle B. Tracy Jr. By the mid-1980s regulations as to who could prepare returns became too strict and the service was discontinued.

His father only ran the business by himself for about a year. In 1946, after serving in the military, Earl B. Tracy Jr. officially joined the company. The two generations of Tracys shared the duties until 1962 when the elder retired. He died only a year later. His son continued to do business with a staff of one or two to help run the office.

Earle B. Tracy Jr. said he moved the company again in 1973, citing a need for both office and parking space. He purchased a lot up Route 186 about a mile from the barn that had been home to the agency for 28 years. He bought a modular home, installed it on the site and converted it into an office.

In 1985, he incorporated the company for business reasons and in 1989 his son, Paul Tracy, joined his father in running the business. Earl B. Tracy Jr. retired at the end of that year but he remains involved in the agency to this day. He maintains his license to sell insurance and puts in days at the office whenever he is needed.

Paul Tracy was working for the city of New York when he got a call from his father, who said he would be retiring soon. The younger Tracy attended night school in Manhattan to get his insurance license. As far as passing the business along to his son, Earle B. Tracy Jr. said, “we hadn’t really talked about it but I don’t think he’s regretted it.”

In the time that it’s taken for four generations of Tracys to occupy the same position at the head of the agency the nature of the insurance industry has changed significantly. As technologies and lifestyles have shifted over the century so has the agency that protects business and home owners, travelers and farmers. Earle B. Tracy Jr. said the biggest changes between the policies his grandfather issued and those his son sells have to do with what is covered and how

comprehensive it is. “Today’s policy tells you what you’re not insured for. Back then it was what you were insured for,” he said. That means today’s policies are comprehensive, identifying what eventualities are not addressed by the policy, while older insurance was disaster specific.

He dug out some old policies signed by his grandfather that specifically address fire as it might affect a house and barn and livestock. Now, he said, there are homeowner’s policies that include a number of facets. And then there’s insurance for things like condominiums. “You don’t own the  building, but you do own it, but you don’t,” he said. Some improvements are covered and some are considered part of the building as it exists, it all depends on the company.

He said before the industry was computerized in the 1980s the agents actually held the policy for whatever parent company they sold it for. Now the agent does a risk assessment and sends an application to the parent company which takes care of the financial transactions.

At the same time the agency is dealing with fewer companies. He said they are demanding higher volumes from individual agents. That means the agents have to select the companies they deal with carefully because they can only afford to deal with a few given the moderate volume the Winter Harbor Agency handles.

Numerous small agencies in the county have disappeared in recent years but the Winter Harbor Agency is successfully bucking the trend. Earle B. Tracy Jr. said that’s because the agency has the stability of 100 years and four generations behind it.

Paul Tracy said that, like most insurance agents, he hopes that nothing exciting will happen. Excitement leads to big claims.

Earle B. Tracy Jr. said the biggest one in his memory was the 1956 fire that destroyed the Grindstone Inn. The grand building had been the center of the summer colony in Winter Harbor but it had fallen on hard times. He said a couple from Vermont were managing the hotel for the company that owned it. They left in October for Vermont, then changed their minds and went to Florida. A few days later the grand wooden structure was up in flame.

Allan Smallidge said the loss was estimated at $100,000 at the time. The Winter harbor Agency doesn’t have the claim on file but Earle B. Tracy Jr. said he recalled that there was an investigation into the cause of the fire and much speculation.

Of course, fire was the biggest risk for both homeowners and merchants before modern building techniques and fire fighting equipment. Earle B. Tracy Jr. recalled the period in his living memory when the firefighters in the area had only a drum of water on wheels that they could roll to the site of a blaze. The quality of current fire departments make it a lot easier to insure houses in the area, he said. And it’s the regularity of small accounts that add up to make the agency a success.

Small and steady and anchored to the community seems to be the golden rule for the Winter Harbor Agency which has endured so many changes in its century of service under the command of generations of the Tracy family.

“I look at it this way,” said Earle B. Tracy Jr. “It’s come down from generation to generation. It’s unreal for any business to stay in one family that long.” But it is real.