My friend Katherine is a bit of a wild child. So she got a kick out of the fact that we celebrated her birthday last weekend over dinner in Boston’s old Charles Street Jail. After five years of renovations, the historic prison that once held famous inmates like James Michael Curley and Sacco and Vanzetti, and was eventually closed after a U.S. District Court deemed it unfit for prisoners, has been transformed into The Liberty Hotel – a super stylish boutique property that opened last month. I have to admit I was expecting hokey prison themed decor, but was surprised by the tasteful mix of original 19th century fixtures (exposed brick walls, catwalk planks, iron barred doors and windows) and contemporary design (enormous wrought iron chandeliers, murals of purple trees and thistle patterned wallpaper reminiscent of designs from Timorous Beasties).

After making jokes about the restaurant name, CLINK, and the waiters' uniforms (each has a prison number on his or her shirt) we found ourselves unexpectedly wowed by a delicious meal. I was impressed by what chef Isadora Sarto (she spent five years working with Daniel Boulud) turned out of her open kitchen, especially when I learned that because the building is a national historic landmark Sarto has to cook her entire menu on electric stoves and induction heat. Everything is meant for sharing and the wine comes in three unusual tasting sizes: a half glass, one and one-half glasses; and two-thirds of a bottle. We nibbled our way through the dangerously addictive “smackerjacks” – truffled caramel popcorn dusted with smoked sea salt - and crispy fried pork cracklins that had a bit of a kick from lime and Thai basil. Our waiter told us the Liberty Ale-battered Ipswich clams were the best he’d ever had - and he grew up on the Cape. We agreed, and ordered seconds. The caramelized brussels sprouts with bacon lardons won over Kat, who insisted she hated the “little green cabbages,” and our main course, espresso braised shortribs, was so rich and flavorful it left us both in a delightful, gluttonous food haze, which we tried to shake off while watching the Red Sox game at the hotel lounge.

Run by Boston nightclub king Patrick Lyons, the lounge is aptly named Alibi and mug shots of stars like Frank Sinatra hang from the walls. Each photo is labeled with a legal charge (Sinatra's was adultery) and alibi of the accused (Frank said: “The broad was into it.”) The line to get in that night wrapped around the block, a sign that the new concept is filling a gap in the Boston social scene. I can only imagine what will happen when Boston culinary legend Lydia Shire opens her new Adam Tihany-designed restaurant, tentatively called Scampo, at the hotel's street level later this year.