From Prisons to Pints and Pillows: 11 Former Jails Where You’ll Want to Serve Time

After stepping through the iron front door, patrons sip on a rotating selection of 10 craft beers in The Jailhouse Craft Beer Bar in Buena Vista, a scenic Gold Rush town near Denver. The building, with wood paneling and stone interior, dates back to the 1880s and was once a stable and then a jail, transitioning from ponies to prisoners to pints.

Wine may not be the first beverage that pops to mind when you think of Hawaii, but Maui Wine has been producing six varietals of red, white, and yes, even pineapple wine on the slopes of Haleakalā since 1974. A stone building on the 23-acre vineyard now used as the Old Jail Tasting Room dates back to the 1850s when it was built as an office for Captain James Makee. It received the nickname “The Old Jail” as wrongdoers on the former plantation and ranch were held here prior to transportation to county jail. An old pair of shackles remains out of sight underneath the bar.

Housed in a former minimum-security prison near Charlotte that operated from 1929 until 2011, Southern Grace Distilleries brews small batches of whiskey in barrels behind bars. Guests can sign up for tours to see the grounds that include the old guard tower, abandoned cells, and the basketball court where inmates shot the hoops to pass the time while serving time. The more adventurous can take the Whisky Prison After Dark Tour where the only light comes from flashlights.

The owners of Seaside Brewing Company restored the long-vacant brick building that housed the Old Seaside City Jail to brew their craft beer in this small city on the northern coast of Oregon. A keg cooler is in the old drunk tank, with beers with names like Lockup IPA poured from taps mounted on the brick wall for a taste of what the brewery calls “cold, delicious irony.”

A run-down two-story brick jail from the 1920s once housed many an overserved guest for the night. After it was gutted, it became the home of Jailhouse Brewing Company, serving year-round and seasonal beers and ales with names like Conjugal Visit, Alibi, and Incarceration. There are rumors that a friendly ghost named Old John makes an occasional appearance, returning to a place where he spent a night or two locked up for public drinking.

Originally a 10 x12’ wooden structure built in 1833, the Boone County jail was upgraded and moved a few times, serving as a jail in this small city near Indianapolis until 1992 when a new facility was built further out. Now the Boone County Jail Distillery produces whiskey, vodka, gin, and rum with names like Warden’s Reserve Whiskey and Conjugal Visit Rum. The second-floor houses Cell Block 104 Restaurant & Bar where guests dine on Italian fare behind bars in a former prison cell waited on by servers in prison guard garb.

Built in 1851, the Charles Street Jail shut down in 1990 and was transformed into the 298-room luxury property, The Liberty Hotel, located at the foot of Beacon Hill. The jails’ granite exterior, 90-foot-high atrium, and catwalks remain. The restaurant, cleverly Clink, incorporates preserved jail cells into its design, and the bar, Alibi, is in the old drunk tank. A landscaped courtyard was built in the former exercise yard.

This former military prison used by the Soviets, Nazis, and Latvians now operates a visitors center where guests can take tours, dress up in military uniforms, play a spy game, enjoy a Soviet buffet meal, and participate in an interactive show based on prisoners’ lives. The more daring can opt to spend the night, sleeping on a prison bunk and “enjoying” prison food. Sign up for the Extreme Night and you will truly step into the life of a prisoner after signing a statement you agree to possible abuse and disciplinary actions that may include physical exercise and cleaning.

This Alcatraz is in Germany and was once a prison dating back to 1867. A few elements of the prison remain, such as a caged reception area, bars on the windows, and updated jail cells that make up some of the 56 rooms. Some guests even opt for striped pajamas in homage to the prisoners’ garb.

Guests stay in updated, modern Comfort Cells made of former prison cells or Deluxe Cells, created out of former prisoner recreation areas at Het Arresthuis (translation: the arrest house) in the city center of Roermond. Built in 1863, the property served as a detention center until 2007. The Cell Block, with its original cell doors and iron catwalks, is available for party and special events.

This former Norman fortress from 1071 was expanded and a portion of it served as a prison until 1998. It is now Malmaison, a boutique hotel that bills itself as “better than your average prison.” The 38 rooms in the A-wing were created from former cells, complete with original iron doors and high barred windows.