Liberty Hotel: A storied property in Boston

The Liberty Hotel in Boston
Entrance to the Liberty Hotel in Boston

Carefully preserving its history and character, Boston’s Charles Street Jail was repurposed as The Liberty Hotel

I once spent a memorable New Year’s Eve weekend in the Clink. No, it’s not what you might think. Clink is a contemporary restaurant located in the Liberty Hotel in Boston, where my husband and I celebrated the holiday with friends visiting from Italy. The restaurant’s whimsical name and old brick walls with iron bars are grim reminders of the hotel’s storied past.

The Liberty Hotel sits on the site of the former Charles
Street Jail, downtown in the Beacon Hill section of the city. Built between 1848-1851, the jail was maverick in its design and orientation. Part of a reform movement to improve inhumane conditions for prisoners, Gridley James Fox Bryant, one of the most renowned architects of the time, and penal advocate Reverend Louis Dwight collaborated on this innovative project, creating 30 arched windows to bring natural light and ventilation into the facility. The jail’s infamous guest list over the years has included James Michael Curley, Malcolm X, the Boston Strangler, anarchists Sacco and Vanzetti, and Frank Abagnale, Jr. (played by Leonardo DiCaprio in Catch Me If You Can.)

The granite building (one of the best examples of what became known as the Boston Granite Style) was designed in the form of a cross, with four wings spreading out from a central tower. The heavy gray stone exterior looks like an impenetrable fortress, built to last. Some 220 prisoners were housed in single 8×10 cells and iron catwalks along the interior allowed guards to pace up and down to oversee them. Based on the rehabilitation-oriented “Auburn Plan,” prisoners were encouraged to work and mingle during the day before they retired to their cells.

About 120 years later, the institution had become filthy, overcrowded, riot prone, and deemed unsuitable for habitation, even by prisoners. It was then that the residents were moved to a new jail (called the Suffolk County Jail) that opened in 1991 and Massachusetts General Hospital acquired the building with the intent of repurposing its use while preserving it character. This involved saving the stone exterior and other significant architectural elements. The $150 million makeover, completed in 2007, created a luxury hotel with a theme that playfully, but poignantly, reminds guests of the building’s colorful history.

An adjacent 16-story tower was constructed to provide additional space, creating a total of 298 rooms and suites (ranging in size from 400-800 square feet), including 18 within the original footprint of the jail. The iron catwalks have been preserved and converted into three stories of balconies surrounding a soaring 90-foot atrium lobby. Guests enter the dramatic lobby through one of two long escalators from the ground floor street entrance. The hotel’s trendy bar, once the holding tank for inebriates, is now decorated with mug shots and aptly named “Alibi.”

Decorated in neutrals and black, the rooms are modern and comfortable, some with views of the nearby Charles River. Operated by Starwood, the hotel offers Molton Brown toiletries, fine linens, flat screen TVs, and free Internet connectivity.

Screen Shot of a Guest Room
Screen Shot of a Guest Room

The only in-room reminder of the building’s stark history is a subtle design on the black and ecru window drapes. With good food and libations, good company, and Christmas trees suspended upside down from the towering ceiling, spending New Year’s Eve at The Liberty was a unique setting to think about past, present, and future.


The Liberty Hotel, 215 Charles Street, Boston, Massachusetts

Do you know of other unusual hotel properties in the U.S. with storied histories?

This post is part of a LinkUp sponsored by Tom Bartel at Travel Over 50.

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  1. I often ride past this hotel on the subway. Unusual building on the outside. Glad to know what to expect on the inside were friends to need a place to stay while in Boston.

  2. I love your description of The Liberty. Next time I’m in Boston, I’ll at least have a drink at The Alibi! My sister and I used to pop into random (luxury) hotels in San Francisco when she lived there, and rate their lobbies and restrooms, just for fun.

  3. The Loew’s Hotel in Center City Philadelphia is in what was one of the first modern “skyscrapers” in the United States. It was built in 1932 for the Philadelphia Savings Fund Society (PSFS) bank. I worked in the building in the early 1980’s, but have not visited since it was converted to a hotel. It is a National Historic Landmark.

    Our “humane” prison, the Eastern State Penitentiary, in use from 1829 until 1971 is now an un-restored museum and is also a National Historic Landmark.

    BTW, great windows in The Liberty.

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