FREEPORT – Thomas Gregory, 69, of Freeport, passed away May 24, 2024, at home. Tom was born in Schenectady, New York, to Thomas P. Gregory and Katherine M. Gregory.

He attended Notre Dame-Bishop Gibbons High School in Schenectady and St. Michael’s College in Vermont. He went on to work for Sterling-Winthrop Research Institute in Rensselaer, N.Y., as a research assistant.

His brown eyes caught his wife Cindy’s attention at the wedding of his best friend and Cindy’s best friend and they were married a few years later and settled in Schenectady. One year later, their daughter Anna was born.

While dating, Cindy and Tom would vacation in Maine and talked about what a wonderful place Freeport in particular would be to raise children. They took their boat to Boothbay Harbor on one occasion, enjoyed the waters there, and fell in love with Maine. Tom would buy Wooden Boat magazines and dream of working on boats and being on the water.

They decided to move to Maine with their nine-month old daughter once Sterling-Winthrop was bought by Kodak. They left with no jobs and no place to live, but once in Maine, Tom got a job working at Dion’s Yacht Yard in Kittery, where he apprenticed to become a skilled craftsman in varnishing, boat building and paint work.

Tom moved the family to Pine Point in Scarborough, where they enjoyed living at the beach, and where he started his own business, T. A. Gregory Yachworks, and worked on boats all over Southern and Central Maine for many years. His first job was working at Portland Yacht Services in Portland, Maine, and he retired in 2020.

When their daughter Mary was born, the family settled in Freeport. He was offered a foreman position at Rockport Marine, where he worked for a short time and then took a foreman position at Brewers South Freeport Marine to be closer to home. Tom then took a position as a supervisor at Bath Iron Works, but went back to his boatwork a few years later.

Tom enjoyed taking his boat out on the waters of Freeport Harbor and cruising the coast. He liked listening to Spanish virtuoso classical guitarist Andres Segovia, jazz guitarist Pat Metheny, Bob Dylan and The Beatles. He loved playing his guitar and taught their daughter Anna to play. He and their daughter Mary enjoyed many camping trips together.

Tom enjoyed gardening and was experimenting with different grasses, and setting his pails in the spring for making maple syrup. What Tom enjoyed most was being at home, keeping up on the home, and spending time with his family. He also enjoyed going to his friend Steven Leveen’s home in Harpswell to maintain his boats. He always ensured that life with his family was special, and enjoyed celebrating holidays and the achievements of his wife and daughters.

He is predeceased by his mother and father.

He is survived by his wife Cynthia Gregory, and his daughters, Anna Elizabeth and Mary Katherine Gregory, and his three sisters, Maria Conlin, Patricia Savignano, and Katherine Gregory and their families,

He will be loved and missed by his family forever.

A Catholic mass will be held at St. Jude’s Church, 134 Main Street, Freeport, Maine on Thursday, June 6, 2024, at 10 a.m. Burial will follow directly after the funeral at Burr Cemetery at 56 Durham Road, Freeport. A celebration of life will be held at De’Bramble Art Gallery at 16 Middle Street, Freeport, beginning at 12 p.m. Condolences may be shared at http://www.FuneralAlternatives.net

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