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Must-See Classic Boston-Area Restaurants

Real connoisseur of everything old and dusty here. Maybe it's Mad Men rubbing off on me, but I want to make sure while I live in Boston (and before they close) I make it to EVERY area haunt that still has that classic feel.

I'm not looking for old places that have updated themselves and ostracized the white-hairs. I want to the places that still make a mean gin martini (and know that vodka is a poor substitute). Maybe they have London broil or peach Melba on the menu. They're surely dusty, and a bit weather-worn, but still have the spirit of an era that involved more hats and gloves than blue jeans and iPhones. They need not be expensive, just earnest.

These places are a dying breed, and I'd like to check them all out before it's too late. As a non-native, I don't have a good handle on where to find these joints.

Food is important, drinks are even more crucial, but what I really care about is the atmosphere.

Help me relive the past!

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  1. Durgin Park, Locke Ober, Omni Parker, etc.

    1. J.J.Foley on East Brekeley St in the South End.

      1. The Oak Room. Perfect old fashioned atmosphere.

        1. Silvertone feels older than it actually is, but the room is nice in a vintage sort of way (but not cheesy) and the drinks are great.

          1. Yes, Oak Room for sure. Also, if you can get out of town, the Wayside Inn is pretty old and classic. I haven't been in years, but I bet the menu has not changed much, and the atmosphere both inside and out is great. The grounds are beautiful always, but especially at this time of year.

            1. Locke-Ober has quite special atmosphere, but the bartending is merely good.

              Some of the old hotel bars preserve some of this feeling: Bar at the Taj, Oak Bar, The Last Hurrah, Swan's Cafe, and though they're not that old, the Bristol and the Rowes Wharf Bar. Same for some upscale restaurants, though most aren't that old, either: Harvest comes to mind.

              The luxury steakhouses do a version of it, with at least some of the service and 60s-vintage bartending if not quite authentically old atmosphere. My favorite of this bunch is Grill 23.

              Our historic taverns are, well, historic, but most aren't great places for a serious cocktail, safer for beers and highballs, though they can probably pour you a decent martini: J.J. Foley's Cafe (South End), Doyle's, Jacob Wirth's.

              For actual great cocktail craft sans authentic old-time atmosphere, there's a handful of places that can accurately recreate not only what Don Draper drank, but his father, grandfather, and great-grandfather, too: Drink, the bar at No. 9 Park, Eastern Standard Kitchen & Drinks, Green Street, Craigie on Main, and Deep Ellum.


              3 Replies
              1. re: MC Slim JB

                while i won't vouch the bartending, smith & wollensky in the castle is quite the setting. built as an armory in the late 1800s, it was a redo dictated by national historic landmark restrictions. plenty of photos on the walls of how the place looked "back in the day" when members of the regiment used it as library/museum/meeting spaces.

                1. re: MC Slim JB

                  Having seen exactly three episodes of "Mad Men" I have only a vague sense of the show but I did realize that my friends were telling the truth when they said I could be an extra on it without the need for the show's costumer or any coaching. Thus, my first thoughts in response to this query were Locke-Ober, The Ritz---the real one, which now masquerades under another name and which has the third bar version (or is it fourth?) in my lifetime---Jake Wirth's , Oak Room, Doyle's....I agree that Doyle's and Wirth's are more along the beer or boilermaker/Irish coffee line. A martini at Locke-Ober is one of the delights of life, even if the bar is "new". (Somewhere I have one of those little shot-glasses they used to use, with the name etched on it.) And the Ritz has always been a welcoming environment, even if the patrons would have been thrown out for wearing those clothes in the Good Old Days. I am not familiar with many of the newer places since my returns to Boston are no long enough to allow me to wander far from my old haunts. But Locke-Ober's bartenders have always been perfectly sufficient...my needs are limited to those Old School cocktails (I have even had them make a perfectly fine Sazerac...back in the 1970's, no less) so perhaps, in this High-Octane Cocktail World they are no up to par with the Fad of the Moment, whatever that may be. But, for the ambiance I think the OP is looking for, the classic cocktails at the Ritz or Locke-Ober would be just the ticket. The only other venues I can think of off the top of my head are private places that take a pride in not having changed a thing for 80 years.

                  I've not been to the Castle since S&W got it but it was a great place for some parties back in the 1970's....

                  It saddened me when Jimmy's was torn down because one of my favoite things was a whiskey sour by the window when the fog was rolling in.....

                  1. re: hazelhurst

                    smith & wollensky spent over $12 million on the reno. it's gorgeous inside.

                2. Nobody has said Pier 44 yet? Does it get any more old fahsioned than that? (Not that you'd go there for the food or drinks.)

                  2 Replies
                  1. re: the modern serf

                    do you mean anthony's pier 4? they have a great selection of white burgundy and do a perfectly serviceable steamed lobster. and the view is spectacular. the servers and barstaff certainly are old and dusty.

                  2. it's not as highbrow as the other places mentioned, but the Pleasant Cafe in Roslindale should be on your list. It is a time capsule- and awesome.

                    1 Reply
                    1. Unfortunately, in terms of drinks being "more crucial", your premise is a bit flawed. The "old dusty" places no longer make good cocktails. If you were to go into Parker House and order a martini, they would give you iced vodka.

                      To get proper classic cocktails, you have to, ironically, go to newer places who hire bartenders who appreciate the classics. Do a search for "classic cocktail" and you'll find them. JB listed several.

                      If you still really want that old timey atmosphere, I would put the bartending at Oak Room and Locke-Ober (sometimes) above other places.

                      Agree that Silvertone gives a mid-century vibe, and is a good choice, too, even though it is "only" around 15 years old or so.

                      1 Reply
                      1. re: Alcachofa

                        The notion of "iced vodka" as a martini is, well, enough to give one chills

                      2. A few that come to mind:

                        The Last Hurrah, downtown Boston
                        Mount Vernon, Somerville
                        Stockyard, Brighton
                        Corrib Pub, West Roxbury
                        Lewis', Norwood
                        Jimmy's Steer House, Arlington
                        Frank's, Cambridge
                        Pleasant Cafe, Roslindale
                        Wayside Inn, Sudbury
                        Colonial Inn, Concord
                        Jeveli's, East Boston
                        Doyle's, Jamaica Plain
                        Greg's, Watertown
                        New Bridge Cafe, Chelsea
                        Durgin Park, Faneuil Hall
                        La Hacienda, Somerville
                        Finian's, Quincy
                        Cafe Venice, Norwood
                        Campanale's, Braintree

                        I'm not sure these are all must-see, but it gives you some options, anyways.

                        6 Replies
                        1. re: hiddenboston

                          What does it say about me that I'm more familiar with this list than almost any other place listed above?

                          1. re: cgj

                            What does it say about ME that this is only a partial list of places I had in mind? :-b

                          2. re: hiddenboston

                            omg!!! lewis'!!!!! i was stuck thinking boston proper, but lewis' is quite the experience. those paintings! and the lewis burger! it is also quite possibly the darkest bar which i've ever visited.

                            they do use fresh-squeezed-to-order orange juice for screwdrivers.

                            1. re: hiddenboston

                              I've not been in The Last Hurrah since a certain VERY dark day in history (October,1986). Do you think it conveys that "old feel" being sought after? Now that we are post-2004, I suppose I can go back there without horrible memories.

                              1. re: hazelhurst

                                Oh, yes. While I'm not a fan of the food at The Last Hurrah, the combination of old-moneyed rich people, bowls of nuts on the tables, and variety of scotches and gin on the drink menu always make me feel like I'm classy, rich, and old (none of which actually apply to me, though the old part seems to be getting more and more realistic).

                                1. re: hiddenboston

                                  Hmm...it all seems so foreign after all these years...I do still have a matchbook from That Awful Night...and I guess hyou are right but the place never "felt" like the Old World to me. Now, the Ritz bar, especially when one could make the Grand Entrance from the back (they removed that in the 1970's) had those little hotelware silver bowls and the nuts etc, and the ashtrays with the little lion in gold on the bottom...and that Ritz Blue that the new (new money) Ritz owners cannot get right. Well, I'll run by Last Hurrah when I am next in town...I always go to Locke-Ober so I;ll be in the neighborhood.

                            2. Audord hui...whoops that one closed recently. Maison Robert...now a Ruth's Chris. L'Espalier...(yes, yes the food and service are still impeccable), however it is not remotely the same experience since moving.

                              Your thought to go before they close is a good one, so very sad what has gone on with our landmark restaurants. Locke Ober still qualifies IMO as a few posters have suggested. Other than that, there is sadly not much which fits the bill for what you seek.

                              1. Thanks for all of the great feedback! I love the hidden gems mixed in here that are not as popular. HiddenBoston, care to share the rest of your list?

                                The more I've thought about it, the more I've realized that although drinks are all well and good, really the ambiance is what I'm seeking. I've been to a lot of these types of places in other cities that are a shadow of their former selves, but you can still feel the glory, if that makes any sense at all. Those are the best to me. Maybe this cocktail renaissance will help some of these spots find new life.

                                2 Replies
                                1. re: KSquared26

                                  Heh, I'll add a few more:

                                  Lynwood, Randolph
                                  Monte's, Lynn
                                  Sadie's, Waltham
                                  Winthrop Arms, Winthrop
                                  Virgilio's Echo Bridge Restaurant, Newton
                                  Louis' Crossing, Quincy
                                  Denly's, Weymouth
                                  Cronin's, Quincy

                                  1. re: hiddenboston

                                    The Continental on Route 1 in Saugus, Anthony's Pier 4 and The Wayside Inn in Sudbury.