A party, 101 princesses and an eccentric millionaire: Jon Ronson on a mysterious castle – and what it taught him about masculinity in crisis

The Castle at the End of the Forest Road: What One Summer Night in Connecticut Revealed About a Man, a Show, and a Fracturing of Male Identity

Wanderstayfinder.com – In the summer of 2023, a young man named Joel sent his father a set of GPS coordinates and a photograph from the middle of a Connecticut woodland. The image showed a sprawling medieval fortress — drawbridge extended, gargoyles perched along its battlements, an almost excessive number of spires and turrets clawing at a low, heavy sky. Accompanying the photo came a single, bewildered line: “I honestly have no clue what is going on. This is very weird.” Joel’s father, the writer Jon Ronson, would later spend days piecing together what had happened that night, and in doing so stumbled onto a story that reads less like a social anecdote and more like a parable about what happens when a man’s sense of purpose collides with a world that no longer recognizes his script.

The Invitation

The evening had begun innocently enough. One of Joel’s female friends had received a message from a man she had matched with on Tinder that week. The text was brief and oddly specific:

“Castle party Saturday! 3:00pm to whenever. Dress code: Formal. Tell your friends. 18+ to come, 21+ to drink.”

Joel and two companions — including a friend named Cement and a woman named Delaney — decided to tag along. They drove roughly three hours from New York City to the small, unremarkable town of Woodstock, Connecticut, a place that shares its name with the far more famous Woodstock in New York State but bears no connection to the 1969 festival. Their GPS carried them out of town onto a narrow, winding road through dense forest, until it terminated at a pair of heavy iron gates. Beyond them, the castle waited.

The group paused, debated turning back, and then watched as the gates swung open on their own. They crossed the drawbridge and were greeted by three figures: a large black dog, a young blond woman, and the castle’s owner, a man in his early sixties named Chris Mark.

“He had sharp blue eyes,” Delaney recalled, “but glazed over.”

“And he had a cut above one of his eyes,” Joel added.

The dog, fittingly, was called Cerberus — after the three-headed hound of Greek mythology that guards the entrance to the underworld. Mark gestured them inside without explanation.

No Party, Only a Premise

They entered what should have been a grand banqueting hall. It was empty save for a scattering of equally confused young adults standing in awkward clusters. Someone asked where the party was. Mark’s answer was immediate and flat:

“Oh no. I’ve invited you here for a different reason.”

A silence followed. Then, prompted by another question, he laid out the premise of what he called his reality show:

“101 Princesses.”

“I’m the lord. I’m looking for my queen and I’ve got 101 princesses to choose from.”

He turned to the women in the group and invited them downstairs to a costume room. They went. Ronson, recounting the episode, noted that this particular detail struck him as quietly melancholy — the willingness of young people to follow a stranger into the lower levels of a forest castle to dress in medieval gowns. The costume room sat adjacent to what Mark described as his hot tub grotto, which also functioned as a subterranean botanical garden, its whirlpool baths ringed by plants lit in purple. The next chamber housed a pole-dancing nightclub populated with mannequins. Beyond that, racks of extravagant princess attire and a glass display case of tiaras waited.

Mark, it became clear, was far more invested in the women’s experience than in Joel or Cement’s. Still, he handed the men tuxedos. When the women reappeared in their gowns and headpieces, a videographer materialized. They were assured the show, though not yet attached to a network, would ultimately land on Netflix. Filming commenced. A woman who apparently resided in the castle curtseyed and announced, “Yes, my lord?”

Mark grew visibly agitated as the evening wore on, irritated that Joel and his friends were watching rather than participating. What “participating” would have meant remained unclear; they had been told the production was “a collaborative project” open to outside ideas. Joel later speculated that the intended role for the men involved some form of dance or physical performance, though the specifics never crystallized.

The Broader Shape of the Story

Stripped of its fairy-tale trappings, the episode at the Woodstock castle is less about a reality show than about a man constructing an elaborate, self-authored mythology in which he occupies the top of a hierarchy that no longer exists. The lord, the queen, the princesses, the hound at the gate — these are archetypes drawn from a medieval script that modern social life has largely retired. Mark’s project, whatever its production status, functions as a kind of personal mythology: a way to re-inhabit a role of absolute authority in a world where such roles have been dismantled, questioned, or simply made irrelevant.

The fact that young people — some recruited through a dating app, some dragged along by friends — were willing to cross the drawbridge, don the tiaras, and let a videographer roll suggests something about the hunger for narrative, for a story with a clear hierarchy and a defined place within it. In an era of diffuse identity and algorithmic ambiguity, the castle offers a script. You are the lord. You are the princess. You are the hound. The rules are written, the costumes are ready, and the gates, once opened, do not close again.

Joel’s initial text — the coordinates, the photograph, the bewildered “This is very weird” — captures the exact moment when the familiar world ends and something stranger begins. What Ronson found, in reconstructing that night, was not merely an eccentric millionaire’s vanity project. It was a small, strange window onto a broader question: what do men do when the old stories stop working, and they build new ones out of iron gates, purple-lit grottos, and a hundred and one tiaras waiting in a glass case?