With South Portland’s long coastline along Portland Harbor and the River Fore, maritime trades have been instrumental in shaping the history of our city and its neighborhoods. Willard has always been a fishing and lobstering community; Ferry Village has been defined by its shipbuilding history and the many captains and fishermen who have chosen to call it home; Knightville and Pleasantdale/Turner’s Island were also home to shipyards and the homes of many people who made their living in sea-related professions.

Sam Gregory, sitting on the steps of his home at 196 Front St., South Portland. Etta Gregory Watts Collection / South Portland Historical Society

As the South Portland Historical Society continues to document the stories of many individuals and families who played a role in our community’s past, this week we take a look at Sam Gregory. It provides an excellent example of the bravery of those who chose to make a living at sea.

Samuel Gregory was born in 1850 in Souris, Prince Edward Island. He moved to South Portland (then known as Cape Elizabeth) when he was around 14.

In 1877 Sam married Mary Caroline Upton. His wife’s name was Carrie, but her family also called her “Callie”, a nickname used by her grandmother that also helped distinguish her from her own daughter.

Sam and Callie had two daughters, Carrie and Etta. They lived at 196 Front St., on the waterfront in the Ferry Village neighborhood.

Portrait of Samuel Gregory. Etta Gregory Watts Collection / South Portland Historical Society

We’ve already written about two of Callie Upton’s brothers.

George Upton was the sole survivor of the sinking of the fishing schooner Mary Lizzie in 1893. Captain John B. Woodbury and six other men, all from Ferry Village, had taken the Mary Lizzie fishing for swordfish. When the schooner sank in a gale, George survived for 33 hours in the ocean, clinging to the wreckage which he had tied to a barrel. The other six crew members all drowned, including another of Carrie’s brothers, Horace. It was a devastating loss for the community of Ferry Village.

Just two years later, Sam Gregory had his own chilling experience on a swordfish trip. The story was reported in the Portland Daily Press August 1, 1895:

“The schooner Abden Keene, Captain Edward Doughty, arrived yesterday from a swordfishing cruise, bringing a fair amount of fish. The crew learned a very interesting story of an exciting adventure by one of the crew members with a giant swordfish, by which Samuel Gregory almost lost his life. The Keene had been out for three days…when a large swordfish was harpooned. As is customary, Sam Gregory was sent in a dory to secure the prize. He got on very well in his efforts for a time, when suddenly the fish went wild and turned the water white with foam, as he pushed madly towards the boat. Several thrusts were made, but at last with a terrible blow the giant fish stabbed the boat head-on on its quarter. It was a terrible blow and Gregory was thrown several feet in the air and overboard, the sword narrowly missing his leg as it pierced the boat. Gregory can’t swim and thought his last days had come, but the fish gave a mighty blow and snapped his sword and left fourteen inches of it stuck in the bottom of the boat. Fortunately, the movements of the fish pushed the boat towards Gregory, who was struggling in the water, and he managed to pull himself up. It seemed he had seen enough swordfish for a day, but his fishing instinct was strong, and within an hour he landed his marine assassin safely. It was a narrow escape for Gregory, and he won’t forget the experience for many days. He now bears a large scar on his side from an injury received from a swordfish a few years ago.

Portrait of Carrie “Callie” Upton Gregory. Etta Gregory Watts Collection / South Portland Historical Society

It’s hard to believe that Sam Gregory would continue to make a living as a fisherman, especially since he couldn’t swim, but like many others in the Ferry Village and Willard neighborhoods, he would still go back and Again.

In January 1907, he had another near-death experience.

Gregory was a crew member on the fishing schooner Fannie Reed when they were hit by a northeast blizzard. According to a story in the Portland Sunday Telegram:

“The Reed left Portland on Thursday for the offshore fishing grounds and Friday morning at 10 a.m. it set down its trawls. Only one man, the cook, William Hall, remained aboard the boat, while the other six took the dories. At 2 o’clock, the time to pick up the trawls, the dreaded vapor which is worse than a fog because it cuts through clothing and skin like a knife, had hidden the small boats from the ship. The men gathered together, calling out to each other, then guessing that their canoe was unable to find them, they set off in single file towards the lightship. Sam Gregory was the first to leave the line, no one saw him again until it was reported this morning that he had been picked up off Cape Porpoise by the schooner Olive Hutchins. The other five men were all able to make it to the lightship, and the cook managed to get the schooner back to Portland on his own. “At about 3:30 a.m. Friday afternoon, Gregory discovered that he had wandered away from the five other dories he was trying to do the lightship with, and in the hope of making Richmond Island or at least Wood Island, he set his little sail, and with the northeast behind him was driven with a terrific speed. Again and again the wintry seas almost engulfed his little craft, and she was soon covered with ice, while he was constantly forced to refloat her…His mittens were getting wet and to keep his hands from freezing he had to beat them against his body and the sides of the boat.Several times he nearly succumbed to the cold, but realizing the need to stay awake and moving in fear to freeze, he made extraordinary efforts. Eventually, despite all he could do, one of his hands went numb and he knew it was frozen. He approached around dawn and shortly after the appearance of the streaks of roses to the east, the O live Hutchins closed in on the blizzard.

The deck of a fishing schooner. Sam Gregory is the tall man, right, pulling a fish on the ship’s rail. Etta Gregory Watts Collection / South Portland Historical Society

While being rescued, Sam ended up having several fingers amputated. He eventually left the sea and took a job with the William Spear Company on Front Street. He died in 1917 and is buried next to his wife Callie in the family plot of Mount Pleasant Cemetery.

If you have any photos, artifacts or information to share regarding South Portland’s past, we’d love to hear from you. The South Portland Historical Society can be reached at 207-767-7299, by email at [email protected]or by post to 55 Bug Light Park, South Portland, ME 04106.

Kathryn Onos DiPhilippo is executive director of the South Portland Historical Society. She can be reached at [email protected]

The fishing schooner Fannie Reed. Sam Gregory had a near-death experience while fishing on the Fannie Reed in 1907. Etta Gregory Watts Collection / South Portland Historical Society

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