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Lucky's Lounge

355 Congress Street, Boston, MA 02210
(617) 357-5825 Find location!

Photo of Lucky's Lounge, Boston, MA The Prohibition Era, which was a period of time in the 1920s and early 1930s when the consumption of alcohol was made illegal, has always been a source of fascination to some, and the show "Boardwalk Empire" from a few years back really sparked some interest in it. During that era, speakeasies, or well-hidden bars that served alcohol, flourished in many areas, including in major cities such as New York and Chicago. Today, of course, there is no longer any need for speakeasies (knock wood), but some relics from the past have survived, though one of the most famous--Chumley's in New York--closed a number of years back after a wall collapsed during construction and has reopened as a much more upscale spot. And Boston? Well, don't expect much in the way of bars that were former speakeasies, but there are some places in town that have a similar feel, including Stoddard's Fine Food & Ale in downtown Boston and JJ Foley's in the South End, which actually may have been a speakeasy back in the day. There is also another restaurant and bar that has the feel of a speakeasy (and which happens to be the focus of this review), and while Lucky's Lounge in the Fort Point District of the city may not be a truly authentic Prohibition Era watering hole, it certainly does have the feel of such a spot.

Located in the heart of the Fort Point neighborhood of Boston (just across the channel from South Station and the Financial District of the city), Lucky's Lounge resides in one of the area's many charming old brick buildings. The entrance to the place is extremely easy to miss, as there is no prominent sign out front and the space itself is slightly below ground level. Walking down a few steps, patrons find themselves in a surprisingly spacious spot, with a room to the left featuring high-back chairs and bar tables, while another room to the right has large vinyl booths. A bar dominates the middle of Lucky's, more or less keeping the two rooms separate from each other, though one side of the bar has seats in the left-hand room, while the other side has more seats in the right-hand room. There are also some sofas in the back of the restaurant as well as a small fireplace. Dim and sultry overhead lights and a mosaic tile floor add additional character to the place. In addition to its prohibition vibe, Lucky's also has a Frank Sinatra them to it, including a great mural of "The Chairman of the Board" toward the back.

While the atmosphere at Lucky's Lounge has a distinct dive-bar feel, the menu actually nudges into the upscale comfort food category, much like what you might find at gastropubs such as The Biltmore in Newton, Highland Kitchen in Somerville, or The Publick House in Brookline. Appetizers include (depending on the season) deliciously lumpy house-made hummus and grilled pita bread; a classic Caesar salad with garlic butter croutons; fish tacos that are stuffed with haddock and topped with red cabbage slaw; fried Brussels sprouts that come with a zesty buffalo sauce; and jumbo chicken wings that can be had with a white-hot habanero sauce. Meals at Lucky's are similarly varied, with such dishes as (again, depending on the season) perfectly marinated steak tips served with mashed potatoes and grilled vegetables; a creamy macaroni and cheese made with four cheeses and topped with Ritz cracker crumbs (and made even better with the addition of buffalo tenders); beef stew that is made with slow-cooked short rib meat and has sweet-tasting parsnips and mild pearl onions mixed in; tender fish and chips that rival some of the best that you will have at the coastal seafood shacks (and the handcut fries that come with the battered fish are marvelous); The Bird, which is a slow-roasted, half chicken with sauteed spinach and potatoes; and several burger options. The drinks menu at Lucky's is what you might expect here, with all kinds of old-fashioned and modern cocktails offered, as well as a decent selection of beer and wine with the former including some local brews. Entertainment at the restaurant includes live bands and acoustic music, and the Sunday "Sinatra Brunch" is a big draw here.

Lucky's Lounge seems to be able to pull off the "speakeasy" vibe pretty well, perhaps because of its nearly invisible basement location in an anonymous brick building--plus the fact that it is in a section of the city that doesn't see as much foot traffic as some other parts of the city. So if you've been itching to get a sense of what a 1920s-era illegal bar is like, Lucky's sure comes pretty close to that feel.