The name of Heartbreak Hill pertains, in the earliest records of Ipswich, to an eminence in the middle of that town on which there was a large Indian settlement, called Agawam, before the white men settled there and drove the inhabitants out. Ere the English colony had been firmly planted a sailor straying ashore came among the simple natives of Agawam, and finding their ways full of novelty he lived with them for a time. When he found means to return to England he took with him the love of a maiden of the tribe, but the girl herself he left behind, comforting her on his departure with an assurance that before many moons he would return. Months went by and extended into years, and every day the girl climbed Heartbreak Hill to look seaward for some token of her lover. At last a ship was seen trying to make harbor, with a furious gale running her close to shore, where breakers were lashing the rocks and sand. The girl kept her station until the vessel, becoming unmanageable, was hurled against the shore and smashed into a thousand pieces. As its timbers went tossing away on the frothing billows a white, despairing face was lifted to hers for an instant; then it sank and was seen nevermore--her lover's face. The “dusky Ariadne” wasted fast from that day, and she lies buried beside the ledge that was her watch-tower.
Ipswich had a very Old Harry in the person of Harry Main, a dark-souled being, who, after a career of piracy, smuggling, blasphemy, and dissipation, became a wrecker, and lured vessels to destruction with false lights. For his crimes he was sent, after death, to do penance on Ipswich bar, where he had sent many a ship ashore, his doom being to twine ropes of sand, though some believe it was to shovel back the sea. Whenever his rope broke he would roar with rage and anguish, so that he was heard for miles, whereon the children would run to their trembling mothers and men would look troubled and shake their heads. After a good bit of cable had been coiled, Harry had a short respite that he enjoyed on Plum Island, to the terror of the populace. When the tide and a gale are rising together people say, as they catch the sound of moaning from the bar, “Old Harry's grumbling again.”