Insurance Agency in Gouldsboro, Maine


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.

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