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Recommendations for old school/divey/gritty Boston spots - restaurants and bars (w/ or w/o food)

Trying to get off the beaten path with a couple of guests coming into town. I'd like to show them some of old school Boston. Looking for recs for old school/divey/gritty Boston spots. They don't have to be divey or gritty, really looking for a strong sense of place that might make up for shortcomings (if any) in the food. The two places I have on the tentative list are Rinos and Bell Isle Seafood. Thanks in advance.

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  1. A few that come to mind....

    Doyle's, JP
    Santarpio's, East Boston
    The Field, Cambridge
    The Paddock, Somerville
    La Hacienda, Somerville
    Cappy's Tavern, Readville
    Cronin's, Quincy
    Waterfront Cafe, North End
    Costello's, JP
    The Corrib, West Roxbury
    Monte's, Lynn
    The Sevens, Beacon Hill

    7 Replies
    1. re: hiddenboston

      I thought f'sure you were gonna send him to The Penalty Box

      1. re: hazelhurst

        Hee hee! Or King Arthur's in Chelsea.

        1. re: hiddenboston

          Ouch! How cruel...I like it. (Actually I wished I coulda been at The Penalty Box they night they won back the Cup. Doyle's woulda been number two, I think.)

      2. re: hiddenboston

        I like these, but don't get your pick for The Field.

        1. re: rknrll

          Probably more sentimental reasons than anything. (A lot of my friends have hung out there over the years.)

        2. re: hiddenboston

          What about Jake Wirth's? Been there lately? When I'm in town I sometimes have a few there before a Sox game. You get decent beer, don;t get clipped like you do at/in Fenway, and the Green Line is practically right there.

          1. re: hazelhurst

            I was going to add that as well, but I think I got distracted. :-) Yes, Jacob Wirth's should definitely be on the list, IMO.

            Jacob Wirth Restaurant
            31 Stuart St, Boston, MA 02116

        3. Sligo Pub, Somerville
          TC's Lounge, Boston

          2 Replies
          1. re: rknrll

            Bull McCabes, Somerville (formerly Tir na N'Og)
            surprised you didn't mention Regina's Thatcher St.

            1. re: rknrll

              TCs has been discovered by the college/slightly post college crowd over the last few years. Lines are longer, and grittiness has all but disappeared.

            2. JJ Foleys
              Costello's and Galway House in JP
              Halfway Cafe in Dedham

              Galway House
              720 Centre St, Jamaica Plain, MA 02130

              1 Reply
              1. re: trufflehound

                I just wanted to second the Galway--they have a pretty good beer selection and the food can be surprisingly good...

                ...and it's not lacking in gritty.

              2. Charlie's Kitchen and Grendel's Den, , Harvard Square

                Charlie's Kitchen
                10 Eliot St, Cambridge, MA 02138

                1 Reply
                1. re: Madrid

                  grendel's can be overrun with students who have gotten far too sloppy. the one time i went i couldn't believe how messed up people were, and er, not "making it to the bathroom," shall we say.

                2. The Erie Pub, Dorchester
                  The Banshee, Dorchester (sort of fits the bill)
                  Biddy Early's, The Financial District
                  Mr. Dooley's, The Financial District
                  Intermission Lounge, Theatre District (far better than Jacob Wirth's)
                  The Blackthorn, South Boston
                  Flann O'Brien's, Jamaica Plain
                  Brendan Behan Pub, Jamaica Plain
                  Murphy's Law, South Boston

                  There are probably a few hundred or more places. You could almost throw a rock and hit one.

                  Jacob Wirth Restaurant
                  31 Stuart St, Boston, MA 02116

                  Biddy Early's
                  141 Pearl St Ste 1, Boston, MA 02110

                  Murphy's Law
                  837 Summer St, Boston, MA 02127

                  Brendan Behan Pub
                  378 Centre St, Jamaica Plain, MA 02130

                  3 Replies
                  1. re: Guinness02122

                    Sullivan's Tap should be on that list.

                    1. re: pemma

                      The Twelve Bens, JJ's Irish Bar (not to be confused with JJ Foley's), The Sevens, Harp & Bard, Dot Tavern, Aces High, The Connection, Sullivan's Pub, that no name pool bar across from Laboure Center in South Boston, The Playwright, The Green Dragon, Bell In Hand (oldest bar in America) etc...we could keep going until Christmas. And they're all "old school Boston" that caters to the poster.

                      Harp & Bard Restaurant
                      1099 Dorchester Ave, Dorchester, MA 02125

                      Dot Tavern
                      840 Dorchester Ave, Dorchester, MA 02125

                      Twelve Ben's
                      315 Adams St, Dorchester, MA 02122

                      1. re: pemma

                        Ramrod/Machine at 1254 Boylston St. Boston is a true dive bar with the added attraction of leathermen and drag queens cavorting during Red Sox games.

                    2. I'd say Charlie's Sandwich Shoppe on columbus Avenue in the South End. Go for breakfast as they're only open til 2 (i think). Also I think they're closed on sundays too. I recommend the cranberry pancakes.

                      Charlie's Sandwich Shoppe
                      429 Columbus Ave Ste 1, Boston, MA 02116

                        1. re: food_lubber

                          Warren Tavern in Charlestown...

                          Warren Tavern Restaurant
                          2 Pleasant St, Charlestown, MA 02129

                        2. Ditto New Bridge, JJ Foley and Santarpios. Also, Durgin Park, Cantina Italiana (for the retro North End vibe-as long as they haven't renovated since I was last there!).

                          Cantina Italiana
                          346 Hanover Street, Boston, MA 02113

                          Durgin Park
                          1 Faneuil Hall Sq, Boston, MA 02109

                          1. Frank's Steakhouse, Cambridge
                            Mount Vernon, Somerville

                            Frank's Steak House
                            2310 Massachusetts Ave, Cambridge, MA 02140

                            1 Reply
                            1. re: SEH

                              Yes to both! Get the twin lobsters at Mt V or the "sizzler" at Franks

                            2. Pleasant Cafe, Rossie
                              Beacon Hill Pub

                              Is Martin's Townhouse still open?

                              1. Wai Wai in chinatown would qualify.

                                3 Replies
                                1. re: nasilemak

                                  Might be a little scary, especially the lady behind the counter!

                                  1. re: Guinness02122

                                    she is just surly. anyone would be too if they had to work there!

                                  2. Haymarket Pizza

                                    Haymarket Pizza
                                    106 Blackstone St, Boston, MA 02109

                                    1 Reply
                                    1. re: nightsky

                                      Yes. Haymarket Pizza is the best!

                                      Haymarket Pizza
                                      106 Blackstone St, Boston, MA 02109

                                    2. I would second Aces High in Southie and JJ Foleys South End, I would add Hogan's Run in Brighton, Model Cafe and Silhouette Lounge in Allston.

                                      Hogan's Run
                                      8 Lincoln St, Brighton, MA 02135

                                      1. O'Leary's in Brookline. The Corrib in Brookline and West Roxbury.Solid food and much better drink prices than the yuppy bars.

                                        1. Not sure if it is still open............. But I have fond memories of the steak tips at the Quiet Man Pub in Southie.

                                          Quiet Man Pub & Restaurant
                                          11 W Broadway South, Boston, MA

                                          1 Reply
                                          1. re: Chris B.

                                            Unfortunately, they've been gone for a few years.

                                          2. Pleasant Cafe in Roslindale! All the dialect experts in the world couldn't duplicate those waitress' accents. Love that place.

                                            1. Just so happens I've got a list of about 100 of them for you right here! ;)


                                              2 Replies
                                              1. re: pantsbensch

                                                Steve "The Rifleman" Flemmi used to eat at the Busy Bee in Brookline...

                                                Busy Bee Restaurant
                                                1046 Beacon St, Brookline, MA 02446

                                                1. re: melon

                                                  And, at that disgusting, dirty Chinese restaurant that used to be where Island Hopper is now on Massachusetts Avenue between Newbury and Commonwealth. The draperies in the front window had 30 years of dirt on them.

                                                  Talk about improving a spot. Island Hopper must take the prize for that category. Every time I go into Island Hopper I give thanks.


                                                  Island Hopper
                                                  91 Massachusetts Ave, Boston, MA 02115

                                              2. Whitney's in Harvard Sq.
                                                The Middle East Restaurant

                                                While we're at it, let's take a moment to recall the Cambridgeport Saloon, Tommy's Lunch, the Wursthaus, the Beehive (the Harvard Sq diner), the Tasty, Nick's Beef and Beer... ok that's enough

                                                Middle East Restaurant
                                                472 Massachusetts Ave, Cambridge, MA 02139

                                                8 Replies
                                                1. re: jajjguy

                                                  Has anyone mentioned Newtowne in Porter yet?

                                                  1. re: chickendhansak

                                                    Hey, yeah. Newtowne has surprisingly decent pizza.

                                                    1. re: chickendhansak

                                                      Newtowne is another place (a la TCs) that's really spruced up over time. Less townies, more college & not-that-far-out-of-college kids. Fresh coat of paint, newer TVs. It's just a bar that has cheap beer & pizza now, nothing gritty about it.

                                                    2. re: jajjguy

                                                      oh yes, Nick's Beef and Beer. I spent many a night there in college getting the cheap black and white Russians (drinking age 18 then). Did that become Grafton St? Penny, I was never at the pre-Island Hopper, but every time I go I want them to be a bit better.Now that I know the history....ok, ok!

                                                      1. re: Madrid

                                                        I still have part of the Nick's Beef and Beer sign in my garage.

                                                        1. re: hiddenboston

                                                          By the end it was Nick's bee and bee ho. Loved that!

                                                          1. re: yumyum

                                                            "Eef and bee ho", I believe (Google seems to agree). I loved that sign. The location is now Temple Bar.

                                                            1. re: dfan

                                                              You're right of course. I could never quite make it out thru my beer goggles. Thanks for the memories!

                                                    3. I'm surprised no one's mentioned the Plough & Stars yet. Seriously old school, character up the wazoo, decent food, plus live music every night of the week (and some afternoons).

                                                      Plough & Stars
                                                      912 Massachusetts Ave, Cambridge, MA 02139

                                                      8 Replies
                                                      1. re: BobB

                                                        I love Plough & Stars, but hasn't it had serious spiffing up in the past 10 years? Charming but glossily painted...not that I mind that at all. Also serious food spiffing up...food is a bit more than decent, I think. Is that old Cambridge dive up Mass Ave towards Central still there.....the one with the Communist-like signs? Can't remember the name at all...could it be Republic of Cambridge?

                                                        Plough & Stars
                                                        912 Massachusetts Ave, Cambridge, MA 02139

                                                        1. re: Madrid

                                                          Yeah, the Plough is far from old school/divey/gritty.
                                                          People's Republik is still there and still stinks.

                                                          1. re: rknrll

                                                            People's Republik stinks as in it's a bad bar or a bar that smells bad? We would, however, be in agreement on both points.

                                                          2. re: Madrid

                                                            It may have - I don't get there nearly as often as I did when I lived on that side of the river many years ago, and when I have been in lately it's been after dark and the place was mobbed so I didn't pay much attention to the decor. I guess I still carry around the old image of it in my head and superimpose it over the reality.

                                                            Still, I give it props for having survived so many decades.

                                                            1. re: Madrid

                                                              Yeah, they underwent a pretty hefty renovation a couple of years ago.

                                                              1. re: jgg13

                                                                plough definitely has outrun its divey past. heck ~~ the bartenders wear vests now.

                                                                1. re: hotoynoodle

                                                                  Hah, that's a change that's new to me. It's been a while since I"ve been there at night, I tend to go there for brunch as I'm not a big live music guy nor much into paying covers. I know that the last time I was there I noticed a surprisingly booze selection (e.g. rittenhouse)

                                                                  1. re: jgg13

                                                                    give it a shot. it remains a good bar, without pretense.

                                                          3. Bleacher bar looking out on Fenway (try the pastrami and put your name on the list for a window table)

                                                            1. Just went out of my way to eat at Grille 705 near Boston Medical Center (had a Groupon that only cost me $1 - can't figure that one out - but it appeared after I filled out their survey). Definitely old school (no beer/alchohol & only open 7am - 4pm, but everyday) - clean, freshly painted, looks like the delis from 30 yrs ago. Huge amount of good, decent food.

                                                              I'm hoping to return w/my 6' 2'' adult son with the insatiable appetite, lol.