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I Stayed the Night in a Probably-Haunted Prison Hotel

When a convict-inspired booze brand invites you to spend the night drinking pruno (that’s prison wine) in a former jail, well, you go.

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The Liberty Hotel, which is tucked into Boston’s Beacon Hill neighborhood among the Massachusetts General Hospital, dates all the way back to 1851 when it was known as the Charles Street Jail, a prison that held Boston’s notorious convicts – from Malcolm X to the Boston Strangler. The former prison was converted into a hotel in 2007, and entering it still feels like stepping into a prison – with, well, modern amenities and a glass of bubbly at check-in.

Considering that it’s set in a converted jail and surrounded by hospital rooms, it’s safe to say the property has a few resident ghosts and while Boston proper is undeniably packed with history, the old Charles Street Jail is so steeped in stories and history, you can feel it.

When 19 Crimes invited me to spend the night at The Liberty to celebrate and honor the Australian convicts on their wine bottles, I knew I had to take on the challenge. I fall asleep listening to “Forensic Files,” I’ve seen every episode of “CSI,” and I’m the first to share ghost stories around the campfire. It was right up my alley.

The property boasts 298 guest rooms, including a penthouse suite overlooking Boston from the State House in the East around to Charlestown in the North. For the real experience, I wanted to check into one of the 18 rooms in the prison proper (a multi-million dollar renovation took place, adding 289 rooms just outside of the prison itself in an adjoining 16-floor building).

Whether in the tower or the prison, it’s easy to be transported back to nineteenth-century prison life, with artifacts and motives peppered throughout the now-hotel. It’s indeed ripe with potential for ghost hunters.

While my own hotel room didn’t give off any particularly spooky vibes (much to my chagrin), the convict stories I learned by way of 19 Crimes certainly did. The Australian wine brand has built a company honoring the notorious convicts that were sent to Australia by way of England for something called “punishment by transportation” and the spirit of the brand has been influenced by the dark history of Australian colonization.

Between 1788 and 1868, nearly 200,000 convicts were transported from Britain to various colonies in Australia, with the idea being colonizing Australia would be worse than receiving the death penalty in England. Each of their bottles, which were served and highlighted at the hotel bar, are dedicated to individual convicts from the Australian penal settlements.

The men and women on their labels are not fictional – they were real people who were uprooted, both criminals and scholars alike, including poet John Boyle O'Reilly, who is depicted on the Grenache and Shiraz blend. O’Reilly continued writing on the journey to Australia, only to escape and make the arduous trek to Boston after outwitting prison guards.

Despite their cruel “punishment by transportation,” these convicts helped create and preserve Australia as we know it today. That is why 19 Crimes and The Liberty Hotel honor their spirit through wine, and continue to be influenced by the principles they lived by.

If you find yourself at The Liberty Hotel, drop your bags and immediately head to Clink for chef Anthony Dawodu’s tasting menu in the converted cells. Clink also boasts an impressive wine list that highlights the convict-inspired wines.

In the mood to stay in and ghost watch? We recommend grabbing a bottle of 19 Crimes Hard Chard (which is a bold homage to the women banished to Australia) and enjoy some “solitary confinement” in your suite while searching for signs of the supernatural.

Wait, So Is The Liberty Hotel Really Haunted?

While I didn’t experience anything supernatural during my stay at The Liberty, I was convinced that there had to be stories out there. The former Charles Street Jail shuttered due to its inhospitable conditions, so there had to be some unhappy prisoners still lingering within the walls.

I took to the internet to see if there were any noted ghost stories and what I found, well, let’s just say I’m glad I looked into it after I had already checked out. There are some spooky stories out there.

According to BostonGhosts, The Liberty Hotel is one of the most haunted spots in all of Boston, and multiple guests have reported to catching a glimpse of strange things outside windows, supernatural reflections in hotel mirrors, and unusual activity in the lobby late at night.

Jthorn47, a Tripadvisor user from California, stayed at The Liberty Hotel last spring and said, “My wife was convinced someone was standing outside our window on the 7th floor!”

An article about the haunted jails on HistoryofMassachusetts.org reports, “The decor boasts brick-walled cells and some may catch the glimpse of a ghost of an old inmate. People to this day still report seeing strange phenomena.”

Whether you’re a proud ghost hunter, a history buff, or you simply appreciate a good glass of wine in a beautifully preserved setting, checking into this historic and ominous property will leave you with handfuls of unforgettable stories – whether supernatural or otherwise.

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Kaitlyn McInnis, Khareem Sudlow