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Where to take an older, hard-boiled, eccentric but loveable drinker?

Swankalicious Oct 28, 2011 05:21 PM

My bachelor uncle is coming up from Manhattan. In a nutshell: The guy has lived in the same rent-controlled studio apartment for 40 years, is a huge packrat, smokes two packs a day, and is extremely eccentric and curmudgeonly (yet fun, with tons of great stories). He's coming up to Boston to meet a woman he met online (yes, this is 2011!) and we're meeting the night before for drinks and dinner.
The guy likes to drink. He's definitely an old-school bar type. I'd like to take him someplace for a few stiff cocktails and then a good steak dinner (he's not a very adventurous eater).
Any suggestions are welcome. He's staying in Cambridge, but I have a car and can pick him up and go wherever.

  1. barleywino Oct 28, 2011 07:18 PM

    Davio's if you're looking for old school swanky steakhouse atmosphere. (Just be careful he doesn't fall asleep in the booth)

    75 Arlington Street, Boston, MA 02116

    2 Replies
    1. re: barleywino
      C. Hamster Oct 28, 2011 07:45 PM

      Davios is pretty new school, actually.

      75 Arlington Street, Boston, MA 02116

      1. re: C. Hamster
        barleywino Oct 29, 2011 01:15 AM

        I guess by old school I'm thinking lots of soft leather private booths , dark wood, dark room with soft lights...Davios seems to capture this sense of swanky privacy better than Grill 23 or Abe & Louies... maybe that counts as new school

    2. digga Oct 28, 2011 07:20 PM

      What a hoot! Is he more of a Frank's (NO Cambridge)/Jimmy's (Arlington...been there once..BIG pours and hearty old-fashioned food)/Chateau kinda guy? Or an Oak Bar/Locke Ober type?

      Curious to know where he's meeting up with his date?!

      1. MC Slim JB Oct 28, 2011 07:32 PM

        I have to ask, what do you mean by "cocktails"? Some folks use this to mean "any alcoholic beverage", including beer, wine, and spirits or spirits-based mixed drinks of one kind or another. What does your uncle drink?


        1 Reply
        1. re: MC Slim JB
          yumyum Oct 28, 2011 07:56 PM

          From the description of the guy I took cocktails to mean drinks. Like a Scotch on the rocks. Prolly not angel share styleee.

        2. C. Hamster Oct 28, 2011 07:44 PM

          Take him to the Pour House for some boilermakers and then to Abe and Louies.

          Pour House
          907 Boylston St Ste 21, Boston, MA 02115

          1 Reply
          1. re: C. Hamster
            Bob Dobalina Oct 31, 2011 04:27 AM

            I second the Abe and Louie's suggestion.

          2. yumyum Oct 28, 2011 07:49 PM

            Oh fantastic! MT Vernon in Somerville has your number. Good stiff drinks in a bar that still smells faintly of smoke and then onward to the dining room for basic but solid fare-- steaks pasta scrod and the like. Nothing that will knock your socks off but he'll be comfortable!

            2 Replies
            1. re: yumyum
              hyde Oct 29, 2011 06:14 AM

              yeah, i think the mt. vernon/ franks/ gregs (watertown) is your vibe. possibly foleys in the south end. or doyles in j.p. after a few pops down the block at the drinking fountain or the midway cafe.....not that i have ever been thrown out of....er....i mean, into, any of these establishments.

              1. re: hyde
                threedogs Oct 29, 2011 07:42 AM

                I haven't been there (yet) but I've been told about how good the place is - was going to suggest Greg's in Watertown. You beat me to it, hyde.

                Also - what about Charlie's Kitchen in Harvard Square? Been years since I've been there (will NOT say how many yrs ago I frequented the place!).

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

            2. h
              hckybg Oct 29, 2011 12:32 PM

              If Harvey Pekar (God rest his soul) visited me in Cambridge, we would go to Casablanca, People's Republik, Cantab Lounge, and the Druid, then perhaps Atwood's for some music.

              7 Replies
              1. re: hckybg
                Trumpetguy Oct 29, 2011 01:43 PM

                Gotta take him out for Jazz music though ;)

                1. re: Trumpetguy
                  hckybg Oct 29, 2011 01:57 PM

                  And no yuppies!!

                  1. re: hckybg
                    Trumpetguy Oct 29, 2011 03:03 PM

                    He was a great guy--I spoke to him on the phone a few times :)

                2. re: hckybg
                  katzzz Oct 29, 2011 04:20 PM

                  Long story short, I had the privilege of having Harvey Pekar take me on his own highly idiosyncratic tour of Cleveland in 1993. The itinerary included a yard sale (Harvey was on the lookout for LPs he could possibly resell), lunch at a middle eastern restaurant in the public market, a bookstore warehouse, the cemetery where James A. Garfield is buried and dinner in an eastern european restaurant (might have been Hungarian). I don't think Harvey was into any kind of bar scene at all. But a jazz club, yes, especially if they had someone playing far out stuff. A third stream concert at New England Conservatory or Berklee would have been right up his alley. As far as food, what he wanted was a combination of tasty and cheap. He'd have been happier at, say, the Greek Corner in Cambridge than at Oleana. The bars you mention would be on Harvey's wavelength if he was a drinker, but I don't think booze was one of his interests.

                  Greek Corner Restaurant
                  2366 Massachusetts Ave, Cambridge, MA 02140

                  134 Hampshire St., Cambridge, MA 02139

                  1. re: katzzz
                    Trumpetguy Oct 29, 2011 05:04 PM


                    1. re: Trumpetguy
                      hckybg Oct 29, 2011 06:26 PM

                      Great story, and lucky for both of you to have met him. I can certainly believe he was not a bar guy, though his portrait popped into my head as the OP described the eccentric, packrat, curmudgeonly, story-telling uncle on his way to meet a distant love. I was just walking past the Lily Pad in Inman, and a jazz quintet (or so) was going absolutely crazy--definitely Harvey territory.

                      1. re: hckybg
                        katzzz Oct 30, 2011 06:46 AM

                        You nailed it. Harvey would have loved the Lily Pad.

                3. c
                  cambridgedoctpr Oct 29, 2011 02:34 PM


                  how about the Taj or the 4 Seasons? The Taj really feels old school to me.

                  In Cambridge, Rialto or Craigie might hit the spot.

                  4 Seasons Restaurant
                  361 Reservoir Ave, Providence, RI 02907

                  10 Replies
                  1. re: cambridgedoctpr
                    hckybg Oct 29, 2011 06:27 PM

                    Nice places, but too fancy! He's an old East Village guy, in a new East Village kinda world. Gotta find a dive bar, not a power brokering spot. :)

                    1. re: hckybg
                      digga Oct 29, 2011 08:37 PM

                      Should you take him to Wally's then? Followed by steak dinner....?

                      1. re: hckybg
                        teezeetoo Oct 30, 2011 08:18 AM

                        East Coast Grill - great food, good booze, never too fancy.

                        1. re: teezeetoo
                          C. Hamster Oct 31, 2011 07:39 AM

                          ECG not very old school ....

                          1. re: C. Hamster
                            teezeetoo Oct 31, 2011 02:18 PM

                            really? it's very east village to me and would fit in comfortably there. probably be a sensation in fact, particularly hell nights.

                            1. re: teezeetoo
                              Trumpetguy Oct 31, 2011 02:21 PM

                              ECG does not feel old school nor East Village to me. Great place to eat &/or drink though ;)

                              1. re: teezeetoo
                                C. Hamster Oct 31, 2011 06:27 PM

                                Are you talking about East Coast Grill or Green Street?

                                Because ESG's bright colors and hula skirts doesn't speak of East Village or old school.

                                Green Street
                                280 Green St, Cambridge, MA 02139

                                East Coast Restaurant
                                1456 Dorchester Ave, Dorchester, MA 02122

                          2. re: hckybg
                            cambridgedoctpr Oct 30, 2011 08:21 AM

                            yeah, fancy and old school Boston Brahmin; worth seeing once. It has not changed since i have been in Boston.

                            1. re: hckybg
                              dulce de leche Oct 31, 2011 08:19 AM

                              Cantab. Or Middle East. Both will have people his age, plus a whole kaleidoscope of others.

                              I know you said steak, but if you were going Italian, I'm feeling the Hacienda on this one.

                              Middle East Restaurant
                              472 Massachusetts Ave, Cambridge, MA 02139

                              1. re: dulce de leche
                                Guido Nov 21, 2011 06:08 PM

                                Yeah! The Cantab - both SO and I thought the same thing.

                          3. l
                            LeoLioness Oct 31, 2011 09:51 AM

                            Frank's in North Cambridge or the Mount Vernon in Somerville if you're less concerned with the quality of the food. Both are old-school and neither is remotely upscale.

                            For drinks, I'd also suggest the Cantab.

                            1. p
                              Pegmeister Oct 31, 2011 10:43 AM

                              Probably not too convenient but the Pleasant Cafe in Roslindale might fit the bill.

                              8 Replies
                              1. re: Pegmeister
                                yumyum Oct 31, 2011 11:42 AM

                                Good call Pegmeister -- that's totally in the same wavelength as the Mt Vernon, Frank's, etc.

                                In fact, I went in on Friday night and had the prime rib ($15!) and friends enjoyed the chicken / eggplant parm, the swordfish kabobs, and wings. I really love the place, based on two visits and it feels preserved in amber in the best way.

                                1. re: yumyum
                                  Science Chick Oct 31, 2011 11:55 AM

                                  Don't forget to try Pleasant's pizza too....one of the best pies on that side of the city!

                                  1. re: Science Chick
                                    yumyum Oct 31, 2011 11:58 AM

                                    It looked FANTASTIC!!!

                                    Friends of mine live around the corner and I'm hoping I can persuade them to go to the Plez more often. If not, I might "pre-eat" there in case it's pasta and nugget night again for the kids.

                                    1. re: yumyum
                                      Swankalicious Oct 31, 2011 02:12 PM

                                      Thank you to everybody. I think we'll be drinking at the Cantab and then heading to Abe and Louie's for a steak dinner. He's meeting his new "paramour" at 75 Chestnut (?).

                                      75 Chestnut
                                      75 Chestnut Street, Boston, MA 02114

                                      1. re: Swankalicious
                                        digga Oct 31, 2011 05:43 PM

                                        That sounds like a great plan. Too bad Forest Cafe is now defunct. That would've been a perfect place to take him....Now that I think of it, maybe Plough and Stars would be a good place to take him pre-dinner? Where is Peter O'Malley drinking these days since Forest Cafe closed? That guy is a trip....

                                        75 Chestnut definitely attracts both the old- and new-ly pickled Brahmin crowd, at least when I was there last.

                                        1. re: digga
                                          digga Nov 15, 2011 07:07 PM

                                          This will probably get understandably deleted by the mods, but here's an interesting article....History of Ploughshares (and a little about Plough and Stars thrown in for good measure).


                                          To keep it on topic, I AM curious to hear where you took your uncle, how the date was, etc....

                                        2. re: Swankalicious
                                          hckybg Oct 31, 2011 07:35 PM

                                          Have a great time, Cantab is a lot of fun. I'm not sure when the music starts, but there's always something good or entertaining (except last time I was there on a Thursday, and it was taken over by BC kids playing Britney Spears between sets of the Chicken Slacks--not cool). As my buddy always says, every kind of person in Cambridge is there and they are all dancing with each other (or sitting at the bar with each other).

                                    2. re: yumyum
                                      treb Nov 1, 2011 09:34 AM

                                      The inside has excellent patina!

                                  2. w
                                    Wannabfoode Nov 18, 2011 08:57 AM

                                    I would suggest Wally's if you want something old school in an east village kind of way. Definitely got that vibe, plus the music is always good.

                                    1 Reply
                                    1. re: Wannabfoode
                                      Swankalicious Nov 19, 2011 08:04 AM

                                      Thank ye for the recommendations, loyal Hounds. Uncle breezed into town and we ended up foaming our cups at Trina's Starlight Lounge, of all places. We then shimmied down the street to the East Coast Grill. Both venues seemed to suit him, although I've never eaten a meal that I've loved at ECG -- somehow always manage to order "wrong." Nonetheless, uncle liked the vibe of the neighborhood. We had hoped for Cantab but his date lives near Inman, as it turns out, so it was to Inman we went.

                                      East Coast Restaurant
                                      1456 Dorchester Ave, Dorchester, MA 02122

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