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Most people wouldn’t get excited about the prospect of staying in a building originally designed to house the incarcerated. However, they may not know the history behind Boston’s Charles Street Jail—now The Liberty, a luxury hotel with award-winning dining in the heart of Beacon Hill.  

Built in 1851, the beautiful granite structure is a masterpiece of stone and glass originally designed by architect Gridley James Fox Bryant and Reverend Louis Dwight, a Yale-educated penologist. It was revolutionary at the time for its prison-reform design. Today it’s a Boston Historic Landmark.

In the 1970s, after housing some of Boston’s most notorious criminals, inmates revolted against the substandard living conditions, and by 1990 the last prisoners were transferred to other correctional facilities. The Boston Redevelopment Authority was looking for a new use of the handsome yet formidable structure while preserving its historical beauty. The development firm Carpenter & Company stepped in, offering a vision of an upscale hotel while preserving the finer points of the jail’s historic design. The team studied original architectural drawings to keep to Bryant’s vision of the cruciform-shaped building with Romanesque and Renaissance flourishes, including the octagonal central building that features four ocular wood windows and four radiating wings, each with Palladian windows that span three stories.

The Liberty Hotel

The light-filled interiors of the common spaces remain unchanged to offer guests the flavor of the building’s original use. Iron bars remain but are backlit in soft colors to illuminate the hallways. The original jail’s central atrium is 90 feet high and surrounded by three levels of catwalks and the building’s trademark windows. This central lobby turns into a lively night spot on the weekends, complete with a DJ spinning a range of music from throwback ’80s disco to new pop hits—a great place to people watch and sip a Cosmo.

Jail cells have also been preserved within the hotel restaurant, Alibi, complete with wrought iron bars, original bluestone flooring, and brick walls.. The inmate’s exercise yard is now a private and beautifully landscaped garden. It’s a true hidden gem in the spring and summer months to sit and enjoy a cocktail.

The guestroom interior design is playful with nods to the building’s rich history. Displayed on guestroom walls are shadowboxes of skeleton keys, historic maps of the city, and black and white etchings of Beacon Hill. When booking a room, secure one of the upper floors for the best views of the Charles River and Cambridge skyline. One of my favorite perks while staying at the hotel was access to the exclusive health club Equinox, a short walk across the Boston Common. After getting a workout in, stop in for a coffee and babka, a sweet European braided bread, at Bakey on Tremont Street. The kosher pasteries are delicious and made with the finest kosher ingredients.

The Banks Seafood and Steak on Stuart Street | Photographs by Matt Kisiday

The hotel concierge also offers bubbly upon arrival, dog-walking services, and bike rentals when the weather permits. The hotel is the perfect jumping off spot to exploring Beacon Hill’s Charles Street and its charming Federal-style houses. Grab an umbrella and good walking shoes. Once you start exploring this well-preserved 18th-century neighborhood, you’ll want to try and take it all in.  

libertyhotel.com

Fine Dining in Beacon Hill

The Liberty’s restaurant Scampo (which means escape in Italian) is considered one of the finest dining spots in Boston, offering Mediterranean-inspired cuisine from James Beard Award–winning chef Lydia Shire. A stalwart of Boston’s dining scene, the 76-year-old Shire can still be found in the kitchen cooking alongside chef de cuisine Simon Restrepo and creating dishes such as handmade raviolis, a variety of house-made pasta sauces served over spaghetti, and swordfish, poached chili chicken, or charred duck breast. Another Boston dining destination for foodies is Chris Himmel’s The Banks Seafood and Steak. Chef Robert Sisca’s offerings are off the chart with a raw bar, caviar menu, and elevated New England classics such as clam chowder, Maine mussels, and a lobster bake dinner—as well as a host of steak cuts to choose from. You’ll want to savor every bite. Saltie Girl is another trending eatery just off Newbury Street on Dartmouth. This Back Bay hot spot is a place to see and be seen. It’s also a great place to try a selection of smoked fish, fried clams, scallops, or fish and chips, Burgundy snails, or a spicy king crab roll.

scampoboston.com, thebanksboston.com, saltiegirl.com

Chef Lydia Shire’s pizza at Scampo | Photographs courtesy of the Liberty Hotel

The Titanic Exhibit

While in Boston, visit the Titanic Exhibit at the Saunders Castle at Park Plaza Boston. E/M Group and RMS Titanic, Inc., have curated a collection of more than 250 Titanic artifacts that allow guests to experience the real stories of Titanic passengers and crew. You’ll also experience the meticulously recreated rooms, including the opulent Grand Staircase.

titanicboston.us

The Boston Ballet and the Isabella Stewart Gardner Museum

Head to a performance at the Boston Ballet. This March attend “Winter Experience,” featuring George Balanchine’s masterpieces, Symphony in Three Movements and Mozartiana; Leonid Yakobson’s Vestris; and Claudia Schreier’s innovative Slipstream. The performance runs from March 20–30 at the Citizens Opera House. And if you are an art lover, you’ll want to read Chasing Beauty, a biography of Isabella Stewart Gardener’s life, and then visit the Isabella Stewart Gardner Museum to take in Isabella’s curated collection of art works amassed over her travels to Europe around the turn of the last century. At the time of the museum’s opening, her collection was one of the finest private collections in the United States. The Venetian Palazzo courtyard in the center of the museum is the perfect spot to sit and take in the beauty of the space on a rainy March afternoon.

gardnermuseum.org

bostonballet.org