Back in the seventeenth century a number of Yankee traders arrived in Naugatuck to barter blankets, beads, buttons, Bibles, and brandy for skins, and there they met chief Toby and his daughter. Toby was not a pleasing person, but his daughter was well favored, and one of the traders told the chief that if he would allow the girl to go to Boston with him he would give to him—Toby—a quart of rum. Toby was willing enough. He would give a good deal for rum. But the daughter declined to be sold off in such a fashion unless—she coyly admitted—she could have half of the rum herself. Loth as he was to do so, Toby was brought to agree to this proposition, for he knew that rum was rare and good and girls were common and perverse, so the gentle forest lily took her mug of liquor and tossed it off. Now, it is not clear whether she wished to nerve herself for the deed that followed or whether the deed was a result of the tonic, but she made off from the paternal wigwam and was presently seen on the ledge of Squaw Rock, locally known also as High Rock, from which in another moment she had fallen. Toby had pursued her, and on finding her dead he vented a howl of grief and anger and flung the now empty rum-jug after her. A huge bowlder arose from the earth where it struck, and there it remains—a monument to the girl and a warning to Tobies.
Another version of the story is that the girl sprang from the rock to escape the pursuit of a lover who was hateful to her, and who had her almost in his grasp when she made the fatal leap. In the crevice half-way up the cliff her spirit has often been seen looking regretfully into the rich valley that was her home, and on the 20th of March and 20th of September, in every year, it is imposed on her to take the form of a seven-headed snake, the large centre head adorned with a splendid carbuncle. Many have tried to capture the snake and secure this precious stone, for an old prophecy promises wealth to whoever shall wrest it from the serpent. But thus far the people of Connecticut have found more wealth in clocks and tobacco than in snakes and carbuncles.