Haunted Wisconsin

The Phantom Rider of Pumpkin Hollow

As dusk settles on quiet autumn nights over the south line road near the crossroads settlement of Oak Hill, a few miles south of Sullivan, in Jefferson County, old-timers say an Indian brave still gallops through the gathering darkness, a garland of sliced pumpkin around his neck. High above his head he holds his ancient rifle, a pumpkin speared around its barrel. His fast pony is festooned with even more pumpkin chunks. The legend of the phantom rider begins in Wisconsin’s early pioneer days and bears more than a casual resemblance to Washington Irving’s “Legend of Sleepy Hollow.” Harry Osgood operated a tavern on that road frequented by ox drivers and travelers on their way to Milwaukee. The structure was little more than a log shelter along the rutted trail. Nevertheless, it was a favorite stop. Early one fall evening, an Indian arrived at the tavern astride a lively pinto pony. He was already tipsy when he stumbled into the establishment but demanded more whiskey. Osgood refused. Instead, he gave the brave a number of ripe, bright orange pumpkins. The Indian was delighted, impaling the largest one on the barrel of his rifle. He cut the others into chunks and with some twine draped them around the pony’s neck. Pleased with his work, he set off down the trail. A short way off, pioneer physician Doc Powers was riding toward the tavern after making calls at several homesteads. As he gazed down the trail, he saw the pumpkin-bedecked Indian galloping toward him. The trail was narrow near 167 The Phantom Rider of Pumpkin Hollow the spot where the two met. Powers demanded to pass first but the Indian refused. Instead, he bashed Doc over the head with his rifle. Powers fell from his horse, but what happened next is unclear. One rendering of the legend holds that the physician recovered his senses and grabbed the rifle from the Indian, smashing the weapon against a tree trunk. The young Indian fled across the marsh, and both horses bolted into the forest. Powers knew that men from the tavern would help find his horse. Another version of the story claims the doctor lay unconscious for some time. When he awoke, pieces of the pumpkin littered the road, but the Indian was nowhere to be seen. The doctor’s horse was found a short way off. Whichever version is correct, Doc Powers swore vengeance on the Indian who attacked him. The doctor made his way to the tavern, where Osgood agreed to help him search for his horse. When the pair reached the spot where the attack had occurred, Powers shook his head over the chunks of pumpkin scattered about. He declared that the name of the area really ought to be changed from Pleasant Valley to Pumpkin Hollow. And so it was. The Indian was never again seen at the tavern or anywhere else in the region. Wayfarers, however, frequently reported the ghost of an Indian bedecked with pumpkins galloping up and down the south line road for many years. And, some say, when the chill autumn wind scatters brittle leaves down Pumpkin Hollow, the Indian brave is still seen in his garish costume. 168 Part II: Southern Frights ...