The last prisoners left the Charles Street Jail on Memorial Day weekend in 1990. Seventeen years later the building reopened as The Liberty Hotel, and now you can order a cocktail in the old drunk tank. Boston has plenty of hotels that used to be something else, or that have hosted presidents and movie stars for more than a century. These are the historic hotels in Boston worth walking into, even if you sleep at home.
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The Liberty Hotel
215 Charles Street, West End
The Charles Street Jail was finished in 1851, next to Massachusetts General Hospital. In 1973 a court ruled that conditions there violated inmates’ constitutional rights, and it still took until 1990 to empty it. When it became The Liberty Hotel in 2007, the designers kept the 90-foot rotunda, the catwalks and some of the cells. CLINK. serves dinner where cells used to be. Alibi, the bar in the former drunk tank, has brick cell walls, the original bluestone floors and celebrity mug shots on the walls. The old exercise yard is a courtyard now.
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Omni Parker House
60 School Street, Downtown
Harvey Parker opened his hotel on School Street in October 1855, and the Omni Parker House is still there, in a building that went up in 1927. Boston cream pie came out of its kitchen in 1856, and Parker House rolls followed in the 1860s. Both are still on the menu at Parker’s Restaurant. John F. Kennedy proposed to Jacqueline Bouvier in that dining room, and Malcolm X, then Malcolm Little, worked at the hotel as a busboy in the 1940s. Have a whiskey at The Last Hurrah, the bar named for Edwin O’Connor’s novel about Mayor James Michael Curley.
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The Fed at The Langham
250 Franklin Street, Downtown
The Federal Reserve Bank of Boston built 250 Franklin Street in 1922 and stayed until 1977. The building turned into a hotel in 1981 and became The Langham later on. N.C. Wyeth painted murals for the bank, and they still hang in what is now the Wyeth Room. The Federal Reserve seal is still set into the terrazzo floor at Grana, the hotel’s restaurant. Downstairs, The Fed names its cocktails after currencies and has live jazz on Friday nights.
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Fairmont Copley Plaza
138 St James Avenue, Back Bay
The Fairmont Copley Plaza opened in 1912 on Copley Square, on the original site of the Museum of Fine Arts. Mayor John “Honey Fitz” Fitzgerald, JFK’s grandfather, hosted the opening party. Henry Janeway Hardenbergh designed it, and he also designed the Plaza Hotel in New York. Every president since William Howard Taft has been a guest, and Elizabeth Taylor and Richard Burton came for their second honeymoon. Walk in through Peacock Alley to OAK Long Bar + Kitchen, which has an 83-foot copper bar. From about 1930 to 1945, the hotel had a bar that actually spun like a merry-go-round.
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The Newbury Boston
1 Newbury Street, Back Bay
The Newbury opened in 1927 as one of the first Ritz-Carlton hotels in the country, across from the Public Garden. Bostonians still call it the Old Ritz. During the Depression, its owner kept the guest room lights on at night so the hotel looked busy and prosperous. It ran as a Ritz-Carlton until 2007, then as the Taj, and reopened as The Newbury in 2021. The rooftop is now enclosed for year-round dining over the Public Garden, and the ballroom and Street Bar got their tall windows back.
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Willow and Ivy – Back Bay
65 Exeter Street, Back Bay
The Lenox opened on Boylston Street in 1900, less than a block from today’s Boston Marathon finish line. Enrico Caruso arrived in his own rail car. Judy Garland first stayed there in 1939, on an MGM promotional tour, and in 1965 she lived there for about three months. Suite 423 is named for her and still has its original fireplace and mirror. If you’re not booking the suite, get a drink at Willow & Ivy, the hotel’s restaurant, which has tall vaulted windows and a long bar.