Chronological / Destinations / Hotels & Resorts / Massachusetts / United States

Loving Liberty in Boston After Two Nights in Jail

A recent visit to New England reminded me that much of our country’s early history has a direct connection to the Boston area. No other single city in the United States offers the potential for as many historical experiences as Boston, the true birthplace of our country and the freedoms we have all enjoyed. But before I go too much further, it would probably be best to clear the air about my own freedom and those two nights in jail. To keep my reputation intact, there was no crime, arrest, booking, bail or trial involved. So, here’s my story:

Liberty Hotel, Boston formerly the Boston Jail
Front Entrance of the Liberty Hotel, Boston formerly the Boston Jail – photo Michael Wechsler Photography

Back in 1851, Boston’s city fathers built the cruciform-shaped Charles Street Jail on Beacon Hill, and it became one of the city’s architectural landmarks. After 120 years of housing some of Boston’s most notorious criminals, it became overcrowded and outdated; there was a prisoner revolt in the 1970s and it was finally closed in 1990. After years of discussion about its fate, along with major efforts to secure governmental approvals; a visionary local developer repurposed and re-opened this historical and architectural gem as the luxurious Liberty Hotel, Boston in September 2007.
Quite by chance, I was in town during its opening month and became one its first "inmates." Thankfully, no fingerprints or bail monies were required, and the stunning new accommodations must certainly be the finest of any "U.S. jail."

Working with a generous $150-million budget, a masterful architectural team worked with conservationists to rebuild the original architect’s dream of a dramatic cupola and preserve most of the iconic granite structure – said to be "one of the finest examples of ‘Boston Granite Style’ of the mid-19th Century," The team added all of the facilities and amenities of a world-class hotel into its 20 guest rooms, and into the additional 280 guest rooms constructed in an adjoining 16-story tower.

A touch of whimsy prevails throughout the Liberty Hotel, Boston: the original jail houses a trendy bar named Alibi in the former "drunk tank," and its Clink restaurant features vestiges of jail cells with (open!) barred doors. Over dinner in the Clink, my wife and I noticed that we were sitting next to a rather loud and fun-loving table. We soon realized that Mick Jagger, Eva Mendez and Meg Ryan were part of the group. Our waiter informed us that it was a wrap party for "The Women," a movie produced by Mr. Jagger and starring Ms. Ryan and Ms. Mendez. The food offerings at Clink were first-rate even if the celebrity table appeared to get the best service (which should surprise few).

Now that most of the opening kinks have been worked out, I am confident that the pet-friendly Liberty Hotel with its panoramic views of the city and hidden courtyard garden will soon be one of New England’s most popular and talked-about lodging destinations (hey, where else can you spend a couple of nights in jail and brag about it?).

For details on room rates, special packages, meeting facilities, etc., see: or call 866.507.5245 (JAIL).

Boston Travel Tips:

  1. My number one tip on Boston: You do not need a car in the immediate Boston area (Bostonian’s concur). It’s a great walking city; taxis are reasonable; and the subway system is the best we’ve experienced in years.
  2. Boston hotels, as in many major cities, can be very expensive; so do some research and you should find something within your budget.
  3. Try to pick a time during the off-season when no major conventions are in town.
  4. Book early as rates definitely climb as room availability decreases. For the ultimate "booking" that you can joke about for years, try reserving a "cell" at The Liberty.

For complete info on Boston dining, lodging, coming events, attractions, etc go to:


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