The prospect of a life behind bars should scare anyone straight. The very thought of zero privacy, strictly regimented routines, bad food, violence, unending monotony, the lack of freedom, and (horrors!) the impossibility of travel, day after day after day, for years or decades or a lifetime chills me — a life not lived, but rather a mirthless existence endured. When traveling, however, a look at life on the inside when you know you can freely return to the outside is a different story. Visiting jails around the world proves to be a fascinating experience. Whether they were built to resemble privileged manor houses or bastions of unimaginable horrors, jails provide a unique experience for the curious traveler. And, if you prefer to extend your stay from a couple of hours during the day to an overnight experience, book a room at one of the jails now operating as hotels. These are my favorites.

#1 Eastern State Penitentiary (Philadelphia, Pennsylvania)

Upon arriving in Philadelphia, I went directly to jail, without passing Go, without collecting $200. I reached my destination of my own free will and not under police escort — Eastern State Penitentiary (ESP). This hulking structure, now a massive ruined bastille in the midst of Pennsylvania’s largest city, was the world’s first penitentiary, opened in 1829, as well as the largest and most expensive public structure erected up until that time in the United States. Closed in 1971 and left to rot, ESP opened to the public as a museum in 1994, in a state of halted decay, and has gained National Historic Landmark status. I approached the foreboding fortress-like structure with trepidation, a little nervous chill tingling along my spine. I stepped into the facility whose hub-and-spoke design served as the model for more than 300 prisons across five continents. Radiating from a central tower, cell wings stretch out to the prison’s perimeter, like a giant wagon wheel. The design plan enabled constant surveillance of the entire prison while providing 450 cells with hot-water heating, a water tap, a toilet, and a skylight (the only source of light), as well as individual exercise yards the same width as the cell, accessed via a short door in the rear of the cell through which all but the shortest prisoners had to stoop down to pass through. Privacy — and isolation — reached new levels in this little outdoor space, with walls so high that prisoners couldn’t see over them or communicate with one another, and no two adjacent yards could be occupied at the same time.

Rectangular openings in the cell walls accommodated the passage of food to the prisoners as well as peep holes to observe the convicts. Like today, right from the start the prison was a destination for tourists, including Charles Dickens and Alexis de Tocqueville, whose numbers exceeded those checking out Independence Hall. Visitors — curious strangers — were allowed to speak with prisoners in their cells, yet the prisoners were not allowed visits from friends or family. I wondered how many disguises were adopted to get around that regulation.

As I strolled the decaying halls, sensing the ghosts of the tortured souls who were confined here and almost hearing the caterwauling of the incarcerated who might very well have been driven mad, I contemplated the penitentiary’s mission: not solely to punish, but to encourage the prisoner’s spiritual reflection, modify their sinful behavior, and make him, or her, become penitent. That philosophy, however, reflective of early-19th-century Zeitgeist, didn’t always materialize in benevolent methods, especially for the prison’s earliest prisoners — petty criminals such as purse snatchers, pickpockets, and burglars, who often served two years. For starters, to set corrigible prisoners on the road to spiritual and behavioral redemption, total isolation was paramount so that the guilty could reflect on their sins: Prisoners were kept locked in their cells by themselves for 23 hours per day, with one hour allowed for outdoor exercise or communal work. Whenever prisoners left their cell, the accompanying guard would wrap a hood over their head to prevent them from being recognized by other prisoners. Silence was strictly enforced. Thick walls between cells canceled any cross-prisoner noises or attempts at communication. Guards wore padded shoes when walking the wards. Anyone committing an infraction faced drastic punishments: drenching prisoners in freezing water, outside, during winter; chaining their tongues to their wrists to discourage any sort of struggle; strapping them into chairs with sturdy restraints for days; and, for the worst, throwing this human flotsam into an underground cell with no light, no human contact, and nearly no food for up to two weeks. The isolation method didn’t survive very long, however, as overcrowding forced more interaction as early as 1913, and group therapy arrived in 1967.

What a Kafkaesque nightmare, I thought, as I strolled through the blocks, noting the claustrophobic cells, the crumbling plaster and peeling paint, the rusting bars and bedframes, the surviving barber shop chair that looks more like an electric chair, and the faded red paint of the cross on the gate to the medical ward, which received an operating room nearly a century after the prison was built; until then, surgeries were performed in a prisoner’s cell. A couple of spaces have been restored from their dilapidated state: a synagogue where Jewish prisoners were allowed to pray, and a solarium that was located over the hospital ward to help combat tuberculosis.

When I stepped outside to relieve some of the oppression, I found myself still smothered. The tall and sturdy perimeter walls prevent any sort of view. Back then, prisoners would have seen nothing but sky; today, some of Philadelphia’s skyscrapers peep up over the top. An outdoor bocce court provided low-key amusement for the prisoners, and a greenhouse enabled at least a little fresh produce to accompany their meals. A rusting panel of numbered buttons indicated the electric cell doors that could be operated along Death Row. And a 97’ tunnel under the prison walls, dug by a dozen inmates, facilitated their escape in 1945; another 30 bootless tunnels that were discovered were not so successful and remained incomplete.

Back inside, I headed toward the cell of the prison’s most famous — and most cossetted — inmate. No, it wasn’t prisoner number C2559 — Pep, the cat-murdering dog, who received a life sentence for killing the Pennsylvania governor’s wife’s cat in 1924. Rather, it was gangster Al Capone, who spent some time locked up here — in relative comfort. I peered through the bars of his cells, noting the cabinet radio, a couple of lamps, an area rug, a credenza, and an armchair.

If any of ESP looks a bit familiar, you’d be right. The penitentiary was tapped for nightmarish scenes in the films Twelve Monkeys, Transformers: Revenge of the Fallen, Animal Factory, and Return to Paradise.

#2 Old Town Jail (Stirling, Scotland)

Like part of a set from any Harry Potter movie, the Old Town Jail looms with gloom and doom. I was spending a day in Stirling, just a short train ride from Edinburgh, drawn mostly to see the city’s commanding castle. With that accomplished, I had ample time to wander around more of the city, and that’s when I stumbled upon the Old Town Jail. This huge and seemingly indestructible jail was built in 1847 in response to deplorable conditions in the overcrowded existing prison, deemed by one reformer as the worst prison in Britain. The New County Jail, its original moniker, was built with the same mission as Philadelphia’s Eastern State Penitentiary: to encourage repentance, beginning with its first inmates, a band of petty thieves. Like ESP, prisoners were fed and kept separate at all times to encourage them to expiate their sins, but they did receive education and payment for work, providing them with skills they could use upon release to lead honest, productive lives. And, like ESP, certain punishments were hardly benevolent: Misbehaving prisoners would be forced to turn the handle of a crank machine to scoop up sand and drop it again, an utterly useless and operose activity devised to break one’s physical and mental well-being in a truly Sisyphean style. The worst of the worst ended up in the Dark Room, a tiny corner chamber with a tiny hole in the top, 40’ above, providing the only light. The War Office took over the jail in 1888 and used it as military detention barracks until 1935. Employed as the headquarters of the city’s civil defense volunteers during World War II and then as a storage depot for a confectionary company in the 1950s, the abandoned jail ultimately fell into disrepair. After some restoration in the 1990s that allowed companies to use the space as offices, the jail reopened as a museum in 2015. Today, you can tour the jail and discover the tales of murder, mayhem, misery, and mischief, as well as some beheadings and hangings, that lurked within its walls among its towers and turrets. End it with a more pleasant experience atop the observation tower, with 360° views of Stirling and the surrounding Scottish countryside.

#3 Old Jail and Court of Appeal (Porto, Portugal)

I went to see the Portuguese Center of Photography, but I was equally impressed by the building in which the center is housed, the former Jail and Court of Appeal. Construction of this tremendous and daunting trapezoidal building (with a deceptively cheerful yellow paint job) began in 1767 and took nearly 30 years to complete. Its spaces were divided between the jail and the court. While the court sections received careful finishings, the prison and detention areas were all about security and punitive conceptions—thick granite walls, iron-plated doors, and heavily barred windows. The distribution of prisoners was dictated by gender, social status, the type of crime committed (anything from counterfeit money changers to revolutionaries to infidelity), and the ability to pay for the incarceration, although those guidelines were often ignored, and overcrowding was a persistent problem. I entered the main hall, a small “prisoners’ courtyard” and felt the oppression of the place, what with its barred windows and doors and granite construction, relieved only by a plain skylight above. Over the decades, the building fell into disrepair and did not benefit from any improvements or renovations, and in 1937 the court moved out. The whole building was shut down in 1974, and the prisoners were transferred out. After an extended period of rehabilitation, the building reopened in 2001 as the home of the Portuguese Center of Photography. Exhibits are spread out along passageways and cell blocks, and include an extraordinarily collection of cameras, from the earliest luggage-size instruments to tiny spy cameras, but shockingly few photographs. You may end up enjoying the building itself as much as the center.

#4 Old County Prison and Pre-Trial Detention Center (Helsinki, Finland)

I was relishing my walk around the Katajanokka area of Helsinki, an island neighborhood at the heart of the Finnish capital that not only houses one of the most beautiful churches in the city but also one of the world’s greatest concentrations of Art Nouveau architecture. Despite these two draws and its location just over the tiny bridge that connects it to the mainland and the city’s main harbor, City Hall, and great farmers market, the neighborhood was fairly empty when I was exploring. I came across the Old County Prison and Pre-Trial Detention Center when I happened to peep into an opening in the tall brick wall that surrounds the entire complex. Katajanokka began life in the 1600s with a few fisherman’s cottages, a red brick foundry, and a warehouse. A century later, they were joined by seamen and craftsman, followed by criminals, drunkards, and transients who skulked around the island’s narrow, twisting alleys and frequented its shady inns. Naturally, this was the place to establish a jail. So, in 1837, the prison was built, a white stucco building that still stands today. For half a century, this prison held inmates awaiting their trial and people imprisoned for unpaid fines. Compulsory exercise routines, outdoor activities, and opportunities for study were introduced in 1866. In 1888, the prison was expanded, with three additional brick annexes built in the shape of a cross, in the “typical Philadelphia prison layout.” The original building was converted into the administrative center, while each of the new buildings — among the first buildings in Helsinki to offer central heating and electric lighting — held 164 cells. The prison suffered damage from an air raid during World War II, and in 1946, an escape tunnel was discovered — not to the outside, where freedom awaited, but between a men’s cell block and a women’s, allowing, I supposed, a different kind of freedom. Post-war, conditions improved in the jail, penitentiary was removed from the law books as a form of punishment, prisoners got paid to study, and shackles were banned. In 2002, the prison was shuttered and all the inmates transferred elsewhere. Only five years later, it reopened as a Best Western hotel, complete with the original and restored prison chapel. Today, it’s the Hotel Katajanokka that welcomes you to stay in the thankfully updated old prison cells with either very high or very low windows and that has been winning awards for years. Protected by the Finnish National Board of Antiquities, the hotel’s exterior, brick walls around the property, and main hallway inside cannot be altered. Exposed brick walls in the dining areas, illuminated by hanging lamps that resemble electroshock therapy helmets, and the hallways with staircases in the middle between the rows of rooms suggest what this jail was like before it became a place of comfort.

#5 Old Lewis and Clark County Jail (Helena, Montana)

On my way from my accommodations, the lovely Sanders Bed & Breakfast, to one of the top five historic districts in the United States, I made sure to stop at the Myrna Loy Center for the Performing & Media Arts. I wasn’t there to attend a performance or buy tickets, but rather to see the building where the center is housed: the Old Lewis and Clark County Jail. This terrific building looks more like an elite lakeside belvedere up in the Rocky Mountains. Rather, the magnificent granite structure sits on a corner lot in downtown Helena. Staircases lead up to arched entrances and handsome wood doors with substantial hinges. A rounded corner tower and a second-story terrace would hint at the occupants enjoying pleasant views and a life of leisure rather than a life behind bars. Built in 1894 after Helena residents voted in favor of a new jail by a margin of nearly five to one, the jail survived for nearly a century before closing. That’s when the performing arts center stepped in. Spearheaded by two transplanted Montanans, from New York and Indiana, the effort to save the jail from the wrecking ball that claimed more than 240 structures in downtown Helena during its 1970s urban renewal phase kicked off in 1989 with a gala fundraising event to convert the vacant jail into the performing arts center. By the time the repurposed jail opened in 1991, more than $1.5 million had been raised to see its metamorphosis. Old jail cells were removed, and part of a back wall was demolished to accommodate necessary expansions for the center, which now includes a 250-seat auditorium and a 150-seat cinema. The successful conversion from jail to entertainment venue is a fine example of historic preservation, simultaneously keeping Helena’s past intact while creating its present, and future. It also pays homage to Montana’s First Lady of Film, Myrna Loy, née Williams, who was born 40 miles from Helena and is today buried in the city, not far from the building that will bear her name for generations to come.

Five Runners-up

• Dunedin Prison (Dunedin, New Zealand, 1896)
• Old Allegheny County Jail (Pittsburgh, Pennsylvania; 1886)
• Prisoner’s Gate (Gevangenpoort, The Hague, Netherlands; 1280)
• Old Nelson County Jail (Bardstown, Kentucky; 1819 / 1874)
• Old Town Jail (Georgetown, Colorado; 1883)

Leave a Comment

Have you been here? Have I inspired you to go? Let me know!