Legend Wood

In 1882, the legend of how the Bear Cave got its name was published in the History of New London County, Connecticut:

Not far from 1750, Maj. Israel Hewitt, who lived on Win-che-choog Hill [now called Wintechog Hill], in North Stonington, became a noted hunter, kept a kennel of bloodhounds, and for pastime and pleasure devoted much of his time in hunting these dangerous animals [wolves and bears]. One old bruin, who rendezvoused in an undiscovered cavern in the upper part of the town, became so destructive among the farmers’ herds in that vicinity that Maj. Hewitt was invited to hunt the rascal down and relieve them from so formidable a pest. So the old hunter, on horseback, in regal style, with servants, munitions of war, and a full corps of bloodhounds, started out in pursuit of the dreaded monster. The hounds soon came upon his foraging tracks, and with that heavenly, or at least unearthly, music that nothing but bloodhounds can chant, they followed with unerring certainty the old mugwump to his den. The practiced ear of the major assured him that the game was bagged. So riding up to the place he saw from the tremulous murmur of his dogs that they had a dangerous animal in hand. After examining the mouth of the cavern and in vain trying to induce the hounds to enter (which they could easily have done), he resolved to enter himself and force the old bruin to a fight in his own den.

The major closely examined his rifle to see if it was well loaded, then picking the flint and throwing off his hunter’s rig, he entered the cavern and cautiously crept along upon his hands and knees until he reached its lower chamber. By this time the darkness was all-pervading, except two headlights glaring at him from the farther end of the cavern, accompanied by a terrific growl, that told the hunter that his or old bruin’s time had come. But the major was equal to the occasion. He, raising his rifle and taking deliberate aim, add another glare to the infernal darkness which shook the cavern from its foundation to its summit. Slowly moving backwards, he reached the surface almost stifled with the sulphurous air of the den. Reloading his rifle and lighting a torch, he again descended into the cavern, and at the farther end he found old bruin with his headlights dim, beyond his growling and his howling, — he was dead. He removed the bear, and with the aid of an Indian servant took him on horseback and carried him home and dressed him, but none of the hounds would touch his meat. The site of this cavern, familiarly known as the “Bear’s Hole,” is situated some three miles north of the village of Milltown [now known as the village of North Stonington], and in former years was a famous resort for sight-seers and parties of young people. But a few invading red snakes having been seen guarding its portals, have sent it back to the silence and solitude that it enjoyed in the olden time. (Hurd p. 742)