The Unsolved Murders of James and Iola Hipp
James and Iola Hipp
Discovery of James and Iola Hipps’ vehicle
He almost missed it as he drove by.
The Vermont State Police trooper was cruising down a familiar stretch of road in northern Vermont—Route 2—a windy two-lane road that connects the state’s capital, Montpelier, with St. Johnsbury.
He slowed down, sweeping over the rest stop with his keen eyes.
Route 2 ran along the river valley carved by the Winooski River. The rest stop was in a little slice of land between the banks of the river and the highway.
He pulled into the rest stop, descending a steep incline to get to a flat paved area with a number of parking spots.
He made his way to the back of the rest stop where he had seen it—a car that was off the road—the back end was hovering above the ground, the undercarriage resting on the rocky riverbank. Its wheels were missing. It was a ten-year-old green sedan—reported as both a Pontiac and an Oldsmobile. Its model was never reported, but its year of manufacture was 1959. Regardless, the two cars were similar. They both had long sweeping lines in a pale metallic green. It was the kind of car you see animated in vintage drive-in movie ads. The body was huge, extending beyond and overhanging its whitewall tires—which were now gone.
The circumstances were strange. From a distance it seemed like maybe it was just a junker vehicle that someone had tried to sink in the Winooski River. But as he approached, he realized that was all wrong. Aside from the missing wheels, the car was in good shape. He stared at the license plates, which were from a state 1,300 miles away—the Sunshine State—Florida. Maybe it was stolen, he thought to himself. Or maybe the car was left there by its owner and then the tires had been stolen from the rest stop. But if that were the case, wouldn’t the trooper have known about it? The owner would have filed a police report for theft, no doubt.
Something wasn’t adding up, but he knew he had to get the car out of the rest stop. He called a tow truck driver who had a hell of a time getting it pulled out and loaded up without any wheels. As he was waiting, he called into dispatch and gave them the plate information and the VIN. The office would work on getting in touch with the Florida Department of Motor Vehicles. He was looking for help tracking down the owner of the mysterious green sedan.
It came back as belonging to James and Iola Hipp from Lutz, Florida.
The car was taken to Brook’s Esso station—Esso was a gas and service station chain.
But where were the Hipps?
He decided to wait and see.
Discovery of the bodies
Two days later, on Friday, September 19th, 1969, two locals—Raymond Orr and Paul Singleton—went to the Vermont State Police barracks in Montpelier to alert them about a seemingly abandoned camper they had found. Raymond’s brother, Harold, owned some land in Calais, Vermont, and it was on his property that they had seen it.
It was the style of camper that was towed behind a vehicle. It was large—24 feet long—but just tall enough to stand up straight. It was a spitting image of the 1960s—a bubbly sheet metal box similar in look to an Airstream—but it was painted green and white rather than left a raw metallic silver.
They estimated that the camper had been there for about a week. They said it appeared that someone drove the camper onto their unpaved land, unhitched it, and drove off in their vehicle.
But it wasn’t until they told the police one final detail that their ears really perked up: they said that the camper had license plates on it from Florida. Immediately things started to click into place. Two abandoned things from Florida in rural Vermont in a matter of a few days? Seemed an unlikely coincidence.
Police followed them to the site. It was just before 6:00PM and the sun was hanging low in the sky. The roads became increasingly more desolate as they left the familiar and well-traveled roads near Montpelier. It was a hilly 8-mile drive into the woods of Vermont.
The troopers took in the scene—it was as they described—the trailer sat quietly in tall grass and low bushes. Behind the trailer rose the slopes of Blueberry Hill, a 1,500-foot wooded summit. Fall was in the air—the highs that day were just 59 and it would dip into freezing temperatures overnight. But the tranquility of the picturesque scene was about to be shattered.
They smelled it before they saw it. As they approached the camper, they began to catch whiffs of a foul odor. By the time they got to the door, it was oozing out of every seam of the camper’s sheet metal body. The door was unlocked. They opened it and the smell was overpowering.
It was warm and stagnant inside the trailer—an airless box that had been fermenting for a week with two bodies inside. It was a gory scene with blood spattered over the walls and floors. A woman who looked to be in her 60s was completely naked and lifeless. A man of a similar age was clothed and laying nearby. The two of them had extensive wounds to their heads and upper bodies—the cause of death was not obvious to the cops nor even the medical examiner who would later respond to the scene. They later described it to the press as “extremely brutal” and a “severe beating.” Without ever divulging the specifics, they said that the woman had been carved in a peculiar way with a knife.
The scene seemed like a moment frozen in time. It appeared the older couple was eating when the intruder entered. On a small table was a plate with a half-eaten sandwich. On another plate was some corned-beef hash. There were condiments—a jar of mayonnaise, a jar of crunchy peanut butter, and a jar of pickles—sitting out. A woman’s blue sweater had been draped over the back of a chair. In a corner was a dish containing dog food. Other than the butter knife on the floor, it didn’t appear to the troopers that there were any signs of a struggle. Despite the obvious violence in front of them, they were struck by how tidy the rest of the camper’s interior appeared to be. In the tiny bedroom was a small bed, neatly made, with a white tufted comforter.
The murder weapon, whatever it was, didn’t appear to be left at the scene. They looked around and found mechanic tools, an axe, and a couple of fishing tackle boxes loaded with fishing gear.
They found a wallet, which was described as “empty,” on the floor of the camper. But they also said that the wallet aided in identifying the victims as James and Iola Hipp from Lutz, Florida.
The Hipps had two things that would prove very valuable to the investigation: One, a detailed log of their daily activities; and two, some rolls of undeveloped film.
Around 9:00PM, the family of the victims in Florida were notified that James and Iola had been murdered. They started immediately making arrangement to come to Vermont. They told the cops that they had expected James and Iola home any time—that their one-month road trip was supposed to be coming to an end. It was on those calls that police learned for certain that there were two dogs that James and Iola had taken with them, but there were no signs of the pups at the crime scene
James and Iola Hipp
James and Iola were already riding high from their trip to Mexico when they decided to embark on another epic adventure. They had just purchased a 24-foot-long green and silver tow-behind camper. It was a little older, but James was handy and gave it a little bit of TLC, getting it ready for a month-long trip from Florida up to Canada and back.
James’s sister, Mary, had recently taken a similar trip and the one who gave them the idea.
They piled their two dogs—a poodle named Missy and a terrier named Lady—into their car, hitched up the camper, and left their home in Lutz on a sunny summer Florida day—Sunday, August 10th, 1969—one month before they would be murdered.
They made it all the way up to Prince Edward Island, a small province in eastern Canada, and an incredible 2,000 miles from Lutz. They were planning on heading back through Kentucky and then Alabama as they made their way back to Florida.
James Hipp was born in 1902 and he was 67 years old. Iola was born in 1907, and she was 62 years old. James was born in a small town in Georgia and Iola in a small town in Illinois. They had four daughters together (Louise, Claire, Joanne, and Sandy) and ended up settling in the Tampa, Florida area. Iola was an active member of the Seminole Heights United Methodist Church for nearly two decades. She held different leadership positions, and she sang in the choir. She was a meticulous bookkeeper, and it was Iola that was keeping a detailed log of their trip.
The Hipps had not lived long in Lutz, Florida— situated about 15 miles north of Tampa. James had worked at the Railway Express Agency for 18 years as a foreman, and had done mechanic work. The Railway Express Agency, or REA for short, was a major player in delivering packages in the US at the time. They had created a nationwide network of railroad parcel delivery, but it had been fading in popularity since the conclusion of World War 2. James, too, was a long-time member of the Seminole Heights United Methodist Church, and held different leadership positions as well. He was also involved in the local Tampa Masons chapter, called the John Darling Masonic Lodge.
In other words, both James and Iola were part of the fabric of the community of Tampa.
They were in their early retirement years, and this trip was one of the first big adventures.
Reconstruction of their final day
From the developed film and the detailed log, the police were able to reconstruct their final days.
From Prince Edward Island, they came back down through western Maine and cut through the White Mountains of New Hampshire. On the night of Thursday, September 11th, a week and one day before their bodies were discovered, they spent the night in a small town called Lancaster in northern New Hampshire, right on the border with Vermont.
They had no friends or family in the New Hampshire/Vermont region—they were just tourists checking it out.
The next morning, Friday, September 12th, exactly one week prior to their bodies being discovered, they went to the Maple Museum in St. Johnsbury, Vermont, where they bought some syrup. This brought them to Route 2, the road off of which their car would later be found stripped of its wheels and abandoned.
From the Maple Museum, it seems that they drove west on Route 2 toward Montpelier. They pulled over in a small town called Marshfield, Vermont, and got gas for around $0.35/gallon. They got back on the road and pulled into the rest stop just outside Montpelier where their car would later be discovered. It was about noontime, and they had stopped to have lunch. They “staked their two dogs to tethers under some shade trees and prepared a picnic lunch.” A witness recalled seeing the Hipps’ camper around 2:45PM. Police estimated that sometime between 2:30PM and 3:00PM that Friday afternoon, the Hipps were murdered in their camper at that rest stop. Their kids thought that it was likely someone they had offered a kindness to… someone they had invited in… someone that turned out to be a violent predator.
Around 3:00PM, another witness told police that he saw the Hipps’ car and camper being driven north to Calais. The witness said that it looked like they were stuck, so the witness pulled over, intending to offer assistance. Before the witness got to the car, the driver managed to free the vehicle and drove off, but not before they got a good look at him. According to the witness, he was 5ft 11in, weighted about 150 pounds, was in his early 20s, and had long, light-brown hair. He clarified it was not “hippie long,” but down past his ears. The person he saw was clearly not one of the Hipps—he was much younger and appeared to be by himself. The killer, it seemed, had driven the Hipps’ vehicle and camper north while they were dead in the back.
The Hipps were not reported missing during that week. They were a thousand miles from home and planning their route as they went. Their families weren’t missing them yet, and no one was expecting them.
The next day, Saturday, the 13th, their green sedan was spotted back at the rest stop. By Tuesday, a man, who was not believed by police to have any connection to the killer, noticed that the vehicle’s back end was lifted up with a type of car jack called a screw-jack, as though someone had tried to get it to go further down the river bank. He said that the vehicle was locked and the keys were inside—he saw them through a window in the ignition. He stripped the wheels off the vehicle and left, stealing them, later turning himself into police, who did not charge him with a crime.
Police efforts
The medical examiner said in his autopsy report, that “the immediate cause of James Hipp’s death was multiple blunt impacts to the head with skull fractures and bilateral acute subdural hematomas.” In other words, massive trauma to the brain and massive bleeding in the brain. He continued, “The approximate interval between onset and death was less than 10 minutes.” The report by the second medical examiner said that Iola Hipp died of “extensive brain lacerations, depressed skull fractures, and severe crushing force by blunt instrument.” He said that she died instantly. He said that there was “no evidence of sexual assault.” It was later divulged that they believed the murder weapon was a ball-peen hammer—this is the type of hammer that has a flat face on one side and a metal ball on the other.
The killer had made life difficult for the police. The bodies were not discovered for a week—a week of fading memories, of deteriorating physical evidence, of rain washing away tracks. But the Vermont State Police and the Washington County Sheriff’s Department put the full weight of their offices behind the investigation.
Though it’s not clear if it was ever done, the police were looking into the possibility of draining the river completely so that they could search its depths. They theorized that the killer may have thrown something into the river near where the car was found.
They developed the film that left by the Hipps—the last images of them alive. The last shots were of James and Iola the morning of their death at the Maple Museum in St. Johnsbury.
They scrutinized the travel log. At each of the stops, Iola would write down the mileage on the odometer. They compared the final reading of the odometer of the Hipps’ vehicle in their impound with the last reading that Iola had recorded—it was a difference of 34 miles. The last place she had recorded the mileage was when they stopped for gas in Marshfield, Vermont—a small town on Route 2 on the way to Montpelier. The cops drove the route and calculated the mileage to see how it compared. They concluded that the killer had not taken the green sedan any further than necessary. I did my own calculation with Google Map directions (from Marshfield to the rest stop, from the rest stop to Calais, from Calais back to the rest stop) and it added up to 33.8 miles—almost 34 exactly. The cops had a good point.
Though they wouldn’t announce it for a month, the police discovered a valuable men’s ring at the rest area. It had a thick 14-karat gold band, it was size 10, and it had one large flat stone, cut into an oval. It was a plain, light blue-gray, agate. Inscribed on the inside of the band was the number 585, which evidently denotes the purity of the gold (58.5%) similar to karats. Jewelers studied the ring and believed that it likely came from Europe—one jeweler from Burlington thought it could be from Asia or Europe and another from Barre said he had seen similar rings in London. They estimated its value at $50 to $100 (or $400 - $800 today). The police sent images of the ring to the family in Florida, but no one recognized it
Most interesting about the ring was that it was “caked in blood.” Preliminary tests by the Vermont crime lab failed to determine if the blood from the ring matched the blood type of either of the Hipps, so they sent it to the FBI. The blood was so old that it was difficult to do any testing. The FBI came back with disappointing results—they said it wasn’t even blood at all.
The single most promising clue that the police developed was from the camper. They were able to identify and lift two good fingerprints that did not belong to James or Iola.
Other violent crimes
Lorette Baker, October 1969
As they were burying their parents in Florida, police were uncovering another body in Vermont. At 12:30PM that Saturday, 2 young boys who were hunting birds had come upon a headless decomposed body of a woman in the woods, 15 miles south of where James and Iola were left in their camper. It was near the summit of West Hill, a 1,500-foot gently-sloping wooded peak west of Barre, Vermont. Authorities were quick to say that they did not believe that the two incidents were connected, but the timing and location were hard to ignore. The same medical examiner in Burlington who autopsied the Hipps, studied this new cadaver and estimated that the woman had been dead for a few months, and was middle-aged. No missing person report matched this description, and the only clue to her identity that they had was the name on a tag on the inside lining of a brown corduroy coat found at the site which read “L. Baker.” Within a couple of weeks the Barre Police Chief announced that they were looking for a missing woman—Lorette Baker—and two days later, he confirmed that the remains found on West Hill were likely hers. The crime went unsolved.
Doris Baker, 1958
Residents immediately connected that name to another unsolved murder in Barre that had happened ten years prior in 1958. A 45-year-old woman had been found dead behind the counter of a flooring store, her head beaten with a hammer, her body cut in various places, and her throat slit with a particular type of flooring knife, in the dead of winter. The wounds were very similar to the wounds sustained by Iola Hipp. Her name was Doris Baker. Her husband was Leo Baker. His initials—L. Baker—were the same as the ones found in the corduroy coat. The State’s Attorney dismissed the connection, though, saying “It was probably a coincidence and nothing more.”
Hope for the future
Despite the passage of time, I still have hope that this crime could be solved.
This case reminds me a lot of the case of Everett Delano that we covered in December of 2021. Everett was killed in 1966, 3 years before the Hipps. There was a fingerprint recovered from the faucet of the bathroom of the service station where he was working when he was killed, and it wasn’t until 2013—47 years later—that police connected that fingerprint to the killer. The New Hampshire Cold Case Unit submitted the latent print to the FBI database, AFIS, and they got a match to convicted felon, Thomas Cass.
In the case of James and Iola Hipp, if the description of the killer is accurate, he was in his early 20s in 1969, and he would be in his mid-70s today. It’s hard to imagine that someone who committed such a vicious crime so early in their life would not have gotten into criminal trouble again over the years. And if so, a police department would have taken their fingerprints. Depending on the timing of their felony, those prints may have made it to the FBI’s national database. What was once an impossibility due to the laborious nature of manually-matching fingerprints, is now done with the click a few buttons.
So, I leave this story with a question—a question for the Vermont State Police. When was the last time you checked those fingerprints?
If you have any information on the murders of James and Iola Hipp, please contact the Vermont State Police Major Crimes Unit at (802)-244-8781 or anonymously text the keyword VTIPS to 274637 (CRIMES).
This text has been adapted from the Murder, She Told podcast episode, The Unsolved Murders of James and Iola Hipp. To hear James and Iola’s full story, find Murder, She Told on your favorite podcast platform.
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A poodle named “Missy,” owned by James and Iola Hipp (Times Argus)
James and Iola Hipp's residence in Lutz, FL (Tampa Times)
James and Iola Hipp's 24FT tow-behind camper (Burlington Free Press)
1959 green Pontiac Bonneville
1959 Oldsmobile sedan, green metallic
Crime scene - John Lesch, a reporter with Times Argus (Brattleboro Reformer)
Roadblock set up by state police on Route 2 near rest area (Times Argus)
Kimberly Cheney, state's attorney (Times Argus)
Reward offering from Burlington Free Press
Ring found near murder scene (Burlington Free Press)
Sources For This Episode
Mentioned in this episode: the case of Everett Delano
Newspaper articles
Various articles from Bennington Banner, Brattleboro Reformer, Burlington Free Press, Miami Herald, Rutland Daily Herald, Tampa Times, Tampa Tribune, and the Times Argus, here.
Written by various authors including Art Gale, Barbara Backus, Bill Pugh, Bryce McIntyre, George Spangler, Mal Boright, Paul Heller, Rod Clarke, and Sally Johnson..
Online written sources
'James & Iola Hipp' (Vermont State Police), 3/20/2016
'1969: Fear and violence' (Times Argus), 8/29/2016, by Paul Heller
'Obituary, Louise H Frier' (Dignity Memorial), 2/7/2023
'Louise H Frier' (Echovita), 2/7/2023
Photos
Photos from Google Maps, Vermont State Police, Times Argus, Brattleboro Reformer, Burlington Free Press and various newspaper articles.
Credits
Research, vocal performance, and audio editing by Kristen Seavey
Research, photo editing, and writing by Byron Willis
Additional research by Chelsea Hanrahan and Ericka Pierce
Murder, She Told is created by Kristen Seavey.