From Infamy To Luxury: The Evolution of the Old Charles Street Jail

The Old Charles Street Jail is truly an architectural gem that witnessed a remarkable transformation over the years. From its origins as a notorious jail to its current incarnation as a luxury hotel…

The Old Charles Street Jail is truly an architectural gem that witnessed a remarkable transformation over the years. From its origins as a notorious jail to its current incarnation as a luxury hotel, this building has a fascinating history.

The Old Charles Street Jail is located on Beacon Hill and was built in 1851 by architect Gridley James Fox Bryant. Designed the Gothic Revival style, the jail became an iconic feature of the city’s skyline. Its towering presence and imposing facade served as a stark reminder of the justice system’s power and authority.

FAMOUS INMATES

During the time it ran as a jail, Charles Street housed several famous inmates. One of the most renowned inmates was the legendary writer and transcendentalist, Henry David Thoreau (who just featured in one of our last blog posts) . He was briefly incarcerated in 1846 for refusing to pay a poll tax, which he saw as a protest against slavery and the Mexican-American War.

Another prominent figure was Malcolm X, the powerful civil rights leader. During his time in the jail in the late 1940s, Malcolm X, then known as Malcolm Little, underwent a transformation and began his journey towards enlightenment, ultimately shaping his future activism.

And another famous inmate was “Whitey” Bulger. One of the most notorious criminals in Boston’s history, James “Whitey” Bulger was, as we all know, an organized crime boss. In 1956, he was imprisoned at the Old Charles Street Jail for armed robbery.

  Albert DeSalvo, The Boston Strangler
  Old Charles Street Jail

In 1973, the Old Charles Street Jail stopped operating as a prison due to deteriorating conditions and concerns over inmate welfare. The building faced an uncertain future until a visionary plan emerged to breath new life into its walls.

Following a long renovation project, the jail was reborn as the Liberty Hotel in 2007. The transformation preserved much of the building’s original architecture, including the iconic central atrium, cast-iron catwalks, and distinctive cell doors. The preservation efforts expertly merged the past and present, creating a unique experience that is also somehow sad considering the suffering that surely happened there.

  The Liberty Hotel

The Liberty Hotel is an emblem of luxury in Boston. The building’s 298 elegantly designed rooms and suites blend modern comforts seamlessly with the jail’s original features.

The former exercise yard has been transformed into a beautiful outdoor space, now known as The Yard, where visitors can chill. The hotel also has the award-winning restaurant, Clink. Plus, huge parties and social events are the regular at the Liberty. .

LEGACY

The Liberty Hotel stands as a testament to Boston’s ability to preserve and repurpose its iconic structures, breathing new life into them while honoring their past.

Have you been to The Liberty? What did you think? Let us know in the comments!

Michelle McCormack

Michelle McCormack

Michelle is founder of Secret Boston. She is a media strategist and creative director. Fun fact: she was once chased by a lion in Africa while on a photo shoot for Town & Country Mag. (It’s been all uphill since then!) Her work spans media, politics, and emerging tech, from early crypto and NFTs to AI today. She’s lived in four countries and five cities, but deep down she’s always from JP.

3 Comments

  1. Sue

    Sue · November 12, 2024

    Loved it today! First time there for lunch at The Clink!
    I Would love me to see more black and white vintage photos on the entry!

  2. Virginia

    Virginia · September 23, 2025

    We stayed at the Liberty a couple weeks ago and had lunch several times at the Clink, the food was amazing and the hotel staff were very helpful, especially the concierge Mark, cannot say enough good things about him.

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