Established in 1836 during the same period of time in which the Wisconsin Territory separated from the Michigan Territory, the soon to be area of Jefferson County, WI, was itself in the process of breaking away from the larger Milwaukee County. Three years later after a successful separation in 1839, the new county, which covers a total area of only 583 sq mi and sits about midway between both Madison and Milwaukee, was officially recognized by territorial legislation and was provided with a county government. Then, only 9 short years later, Wisconsin itself would be granted statehood and would officially become the 30th state admitted to the Union.

Within the borders of Jefferson County, small cities such as Fort Atkinson, Jefferson, Lake Mills, Waterloo, Watertown, and Whitewater flourish. Among these cities, many monsters are believed to flourish as well (that is if you believe the stories). Creatures such as the Lake Ripley Monster, the Lake Koshkonong Monster, and Rocky The Rock Lake Terror, are all believed to call this area home alongside the many locals. But these feared lake serpents are not why we are here today. In fact, we are not going to be talking about monsters at all this time around. The main reason for this article is to talk about an occurrence that is believed to have taken place nearly 200yrs ago within Jefferson County, and one that is still spoken about today within small groups that are few and far between. Dear readers, we are here today to talk about a Pumpkin Wielding Rider.

As mentioned above, Jefferson County holds within its area some pretty recognizable cities to those within the state, many of you may even recognize Whitewater right off the bat due to its UW College System affiliation. But outside of these cities, many villages and communities go unnoticed. Did you know that officially within the county, there are 5 villages, 16 towns, 6 census-designated living areas, and 27 unincorporated communities? It’s true. That leaves the door open for a lot of areas in which Folklore could arise. And wouldn’t you know it, the area in which this next bit takes place is tallied amongst those numbers listed above.

The unincorporated community of Oak Hill is located about 6mi south of the village of Sullivan, and 13mi east of Fort Atkinson. The community sits at the crossroads of County Road E and Country Road Cl. Now, according to the legend, during the mid to late 1800s (the exact date isn’t clear), there was a tavern located at these very crossroads. The tavern (whose name is lost to history) was a main stop for those traveling between Madison and Milwaukee, who were looking to take a break for a few hours and relax for a bit with a drink. Because of this, all manner of different types of people would frequent the tavern and partake in the spirits served up by tavern owner Harry Osgood. Ultimately though, this constant flow of people would lead to some tension among certain groups due to the issues that were currently going on within the state.

You see, during the mid-1800s, the US government was in full swing of removing the native peoples of Wisconsin from their tribe lands and forcing them onto reservations which it had chosen. This was accomplished through manufactured inter-tribal warfare (the US had manipulated different tribes into war with one another to gain land), as well as broken treaties and failure to maintain peace agreements. Needless to say, things were a bit tense in the area among the Native Americans and European settlers, so it’s not difficult to believe that little altercations fueled by this tension would manifest themselves in various locations around the county. And what better location is there to bring out this tension between two people than at, you guessed it, a tavern.

The legend claims that on one fall evening, while Harry Osgood was going about his daily routine, a Native American man (of either the Ho-Chunk or Potawatomi tribe) on horseback arrived at his crossroads tavern. Upon entering the wooden structure, the man approached the counter and requested a whiskey from Osgood. Some tellings of the legend claim the traveler was already quite tipsy when he arrived at the tavern, while other tellings claim Osgood just didn’t want him in there due to the recognized tensions mentioned above. Either way, Osgood refused to serve the man the alcohol he requested.

Obviously annoyed at the lack of service he was receiving, the traveler refused to leave the establishment until he got something. Still firm on not giving the man whiskey, Osgood had the visitor follow him around out back to show him what he could have. There, scattered across the grass and around the tavern, were a large number of pumpkins. Osgood told the Native American traveler that he was free to take as many pumpkins as he wanted, but regardless if he did or not, he would have to be on his way.

The Native American stared at the pumpkins for a moment and then walked back around the tavern disappearing from view. Osgood, figuring the man had decided to leave, turned around to head back upfront when the man reappeared with his horse in tow and a rifle on his shoulder. The traveler approached the largest pumpkin among the bunch and, with eyes staring at Osgood, thrust the barrel of his rifle into the orange mass, lifted it off the ground, climbed onto his horse, and rode off down the crossroads. Osgood watched as the Native American rode towards the setting sun on the horizon until he eventually faded from view. Happy he was finally gone, the man returned inside and prepared for the next visitor.

Not far from the crossroads, a traveling doctor was making his towards the tavern after completing his day’s work. The sun had disappeared from the sky and the cool autumn night had taken over the area. Fallen leaves from the trees actively preparing for winter slid across the road while their branches moved back and forth in the wind. The doctor, taking notice of the chill in the air, instructed his horse to pick up the pace in hopes of reaching the tavern soon to warm up and possibly partake in a drink.

The area, now fully engulfed by the night, took on a spooky appearance as the duo continued on towards the crossroads. The entire ride had been a leisurely one down the long stretch of road hugged tight by both trees and crops on either side. The doctor had encountered no travelers and found it strange at first, but quickly chalked it up to the time of night as well as the crisp chill that had filled the air. With only a short distance remaining between him and the tavern the doctor continued on. Only a few more minutes until he was inside the warm building and off the back of his horse. But then, something strange appeared down the road in front of him.

The doctor, obviously intrigued by what had stepped out onto the road, once again signaled for his horse to pick up its pace. The temperature was continuing to drop and the doctor had had enough of the cold. As his horse started to gain a bit of speed, the object in the road began to move as well. And it was coming directly down the road towards him. The doctor squinted his eyes and attempted to make out what was moving in the darkness. From what he could tell, it was a man on horseback, but they had some strange object resting on their shoulder which the doctor could not verify. The doctor called out for the man on horseback to move out of the center of the road and let him pass, but the unknown rider continued forward. The doctor once again yelled out for the stranger to move so as they didn’t run into each other as they neared. Still ignoring the doctor’s call, the rider instead signaled for his horse to run at a full gallop.

The doctor yelled for the man to stop as they would inevitably soon collide, but it was no use, the rider it appeared was determined to hit something. Quickly signaling for his horse to stop, the doctor attempted to move out of the way, but the other rider was moving too fast. The doctor, now clearly seeing that this stranger was a Native American man on horseback, no longer had to squint his eyes to make out what appeared to be resting on the man’s shoulder. As the rider charged his horse forward, the doctor watched as he raised a rifle high in the air and swung it forward like a club. A large pumpkin, speared through the center by the barrel, smashed into the doctor’s head and knocked him from his horse. He fell to the ground with a hard thud and landed in the dirt. With his head pounding and his eyes beginning to gloss over, he recognized that he was starting to lose consciousness. But before he did, he watched as the Pumpkin Wielding Rider reared up on his horse, thrust his rife into the air, and let out a yell. Then, as he expected, everything went black.

When the good doctor awoke sometime later in the middle of the road, his body was frozen and bits of pumpkin guts had taken up residence upon his head and within his clothing. The shell of the weapon lay scattered amongst him in pieces, the orange color noticeable in the moonlight and the white seeds easily seen along the ground. With wobbly legs, the doctor rose to his feet. He scanned the surrounding area for his horse but it was nowhere to be seen. Not wanting to remain in the cold any longer, and desperately needing a stiff drink to combat his pounding headache, the doctor made his way towards the tavern.

Upon arriving at the establishment, the doctor made quick work of relating what had happened to him. The patrons inside listened with wide eyes and stifled laughter as the doctor described how it felt to be hit in the head with a pumpkin. One person who wasn’t laughing though was Harry Osgood, he believed the good doctor right away because he knew exactly who was responsible as well as where the attacker got his weapon from. The doctor asked Harry if he would by chance help him look for his horse as it was his only means of travel. Osgood agreed and later the two men stepped outside to search.

When they arrived at the spot of the attack, pieces of destroyed pumpkin were still scattered across the dirt road. The men searched the area and called for the doctor’s horse, and surprisingly, they managed to find it. The animal was located in the surrounding treeline with zero injuries and completely void of pumpkin guts, unlike its unfortunate owner. What wasn’t able to be located though was any trace of the pumpkin wielding rider. It was as if he simply vanished into the darkness and was never seen again. The story of the pumpkin attack on the doctor spread around the area quickly, and those traveling the road kept a watchful eye in case the attacker should ever come back, but he never returned. His story quickly transitioned from a warning to a legend and the Pumpkin Wielding Rider unsurprisingly became a new folklore character.

But the story doesn’t end there, not at all. You see, with most characters of folktales, their legends continue to grow as time goes by. As the story gets told and retold and passed on and told again, new pieces get added to the overall story. The Pumpkin Wielding Rider is no exception to this rule because somewhere down the line, the rider was transformed into a phantom. People in the area started to claim that on cold autumn nights, you can still see the rider galloping down past the crossroads with his rifle and pumpkin in the air and a wild scream echoing out into the surrounding area. As quickly as he arrives he disappears like a ghost and for a few moments afterward, you can see pieces of pumpkin scattered across the ground before these too fade from view.

Nobody knows why or when the rider became a ghost, and nobody can explain why it chooses to repeat its pumpkin attack on random nights. There is zero evidence to prove that the phantom rider exists in any real capacity, yet people just accept it as is because that’s how the story tells it. This though opens the door to a whole new issue, you see, just as there is no evidence that the phantom rider exists, there is also zero evidence that the actual Pumpkin Wielding Rider story took place as well. Sad to say, but this entire story could be nothing but fiction. Now you may be asking, “PBI, what evidence do you have that this didn’t actually happen?”, and to that I say, we don’t have any evidence! But what we do have is recorded history, as well as a little story that you might have already heard of. A gothic tale written in 1820 by American author, Washington Irving. A short ghost story widely known as, and you’ve probably already guessed it, “The Legend of Sleepy Hollow.”

For those of you unaware of the nearly 200yr old story of Ichabod Crane and the Headless Horseman, please take a moment to catch up with this extremely brief summary. The story follows schoolmaster Ichabod Crane after arriving in the secluded glen of Sleepy Hollow. While there, he tries and fails to win the hand of Katrina Van Tassel, sole daughter of the town’s wealthiest farmer, Baltus Van Tassel. Another man, Abraham Van Brunt, is also attempting the same thing, to win the girls affection. Van Brunt, not wanting any competition for Katrina’s hand, plays a series of pranks on Ichabod as well as fills his head with various legends and ghost stories regarding the surrounding area. One of these stories happens to be about the legendary Headless Horseman, a Hessian trooper who lost his head after being struck by a cannonball during the American Revolutionary War (1775–1783). His body was said to be buried in a plot within Sleepy Hollow and every so often, he would rise from his grave as an angry ghost and furiously search for his missing head.

One night, after leaving a party put on for the town by the Van Tassel’s, Ichabod finds himself alone while traveling in a section of supposedly haunted woods. While in said woods, the schoolmaster comes face to shoulders with the infamous Headless Horseman. The ghost is described as wearing an all-black uniform with a long flowing black cape and is seated upon a large, black, red-eyed stallion. It is also said to be carrying what appears to be a severed head. Ichabod and his horse take off at full speed towards the one location the Horseman is unable to venture, the bridge in front of the Old Dutch Burying Ground. Sadly though, Ichabod is too late and the Horseman whips his severed head at the schoolmaster, knocking from his horse and sending him into the dirt.

The next morning, Ichabod Crane is nowhere to be found within Sleepy Hollow and because of this, Abraham and Katrina soon marry. When the residents of the glen begin a search for the missing man, all they can find is a discarded hat of his, a ruined saddle, and broken pumpkin pieces scattered around a hectic scene in front of the bridge. The story ends by leaving the reader to decide for themselves if Ichabod fell victim to the Headless Horseman, or if the whole thing was nothing but a prank carried out by Van Brunt to drive Ichabod out of Sleepy Hollow and away from Kristina for good.

As you can see, the similarities between both the Pumpkin Wielding Rider and the Headless Horseman are numerous. So much so that we don’t even feel its necessary to list all those similarities here as the stories speak for themselves. It is because of these similarities, that we believe the legend of the PWR was directly inspired by the story written by Washington Irving near the beginning of the 19th century and was modified by someone to make it more region-specific and easier to relate to by those living in the Midwest at the time. The one final question that ultimately remains though is, why?

Without knowing exactly when the legend of the PWR was created, it is safe to say that this question will more than likely never be answered. And honestly, if you ask us, that’s just fine. We feel there is zero harm in having both an East Coast and Midwest version of a ghost who is just angry all the time and personally chooses to express that anger by throwing pumpkins at slow-moving individuals who get in its way while simply wanting to travel from point A to point B.

So whether the legend of the Pumpkin Wielding Rider is true or not, we feel it’s necessary to give this last piece of advice. If you ever find yourself at a crossroads and a large figure on horseback appears in front of you, just move to the side and let them pass. There is a 50/50 chance this could be a ghost, and honestly, it’s easier to just move for a few minutes than deal with the after-effects of getting smashed in the head with a pumpkin.

-The Pine Barrens Institute

Image Credit: https://www.digitalcommonwealth.org/search/commonwealth:3j333c19f

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