With South Portland’s long coastline along Portland Harbor and the Fore River, the maritime trades have played a defining role in shaping the history of our city and its neighborhoods. Willard was always a community of fishermen and lobstermen; Ferry Village was defined by its shipbuilding history and the many sea captains and fishermen who chose to live there; Knightville and Pleasantdale/Turner’s Island were also home to shipyards and the homes of many who made their living in maritime-related occupations.

As South Portland Historical Society continues to document the history of many of the people and families who have played a role in our community’s past, we take a look this week at Sam Gregory. He provides a great example of the bravery of those who chose to make their 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 about 14 years old.

In 1877, Sam married Mary Caroline Upton. His wife went by the name Carrie, but family also called her “Callie,” a nickname used by her grandmother and which 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.

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

George Upton was the sole survivor of the wreck 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 out to fish for swordfish. When the schooner went down in a gale, George survived for 33 hours in the ocean, clinging to wreckage he had tied to a barrel. The other six members of the crew all drowned, including another of Carrie’s brothers, Horace. It was a devastating loss for the Ferry Village community.

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

“The schooner Abden Keene, Captain Edward Doughty, arrived yesterday from a sword fishing cruise, bringing a good quantity of fish. From the crew was learned a very interesting story of an exciting adventure by one of the crew with a giant sword fish, by which Samuel Gregory nearly lost his life. The Keene had been out three days…when a large sword fish was speared. As is the custom, Sam Gregory was sent off in a dory to secure the prize. He got along very well in his efforts for a time, when suddenly the fish became wild and made the water white with foam, as he thrust madly at the boat. Several thrusts were made, but at last with a terrific blow the giant fish stabbed the boat full and fair on her quarter. It was a terrific blow and Gregory was thrown several feet into the air and overboard, the sword just missing his leg as it pierced the boat. Gregory cannot swim, and thought his last days had come, but the fish gave a powerful lunge and broke his sword short off and left fourteen inches of it sticking in the boat’s bottom. Luckily the movements of the fish pushed the boat toward Gregory, who was struggling in the water, and he managed to scramble in again. It would seem as if he had seen enough of sword fish for one day, but his fisherman instinct was strong, and in an hour’s time he had his marine assassin safely landed. It was a narrow escape for Gregory, and he will not forget the experience for many a day. He carries a big scar on his side now from a wound received from a sword fish some years ago.”

It’s hard to believe that Sam Gregory would keep on earning his living as a fisherman, especially since he didn’t know how to swim, but like many others in the Ferry Village and Willard neighborhoods, he would head out again 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 Thursday for the offshore fishing grounds and Friday morning at 10 o’clock set her trawls. Only one man, the cook, William Hall, was left aboard the boat, while the other six took to the dories. At 2 o’clock, 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 vessel. The men gathered together, shouting to one another, and then guessing that their boat was unable to find them started in single file for the lightship. Sam Gregory was the first to drop out of line, nobody saw him again until it was reported this morning that he had been picked up off Cape Porpoise by the schooner Olive Hutchins.” The five other men were all able to make it to the lightship, and the cook managed to bring the schooner back to Portland by himself. “About 3:30 o’clock Friday afternoon Gregory found he had drifted away from the other five dories with which he was trying to make the lightship, and in the hope of making Richmond Island or at least Wood Island, he set his little sail, and with the northeaster behind him was driven at terrific speed. Again and again the wintry seas almost engulfed his small craft, and she was soon cased in ice, while he was constantly forced to bail her out…His mittens became 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 almost succumbed to cold, but realizing the necessity of keeping awake and in motion lest he should freeze, he made extraordinary efforts. Finally, despite all he could do, one of his hands became numb and he knew it was frozen. It drew on towards daybreak and shortly after the rose streaks appeared in the east the Olive Hutchins loomed close in the driving blizzard.”

While he was saved, Sam ended up having several fingers amputated. He finally 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 at Mount Pleasant Cemetery.

If you have photos, artifacts or information to share related to South Portland’s past, we would love to hear from you. South Portland Historical Society can be reached at 207-767-7299, by email at sphistory04106@gmail.com, or by mail at 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 sphistory04106@gmail.com.

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